Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053273314015599/pc5039sup1.cif | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053273314015599/pc5039sup2.pdf |
CCDC references: 1025038; 1025039; 1025040; 1025041; 1025042; 1025043; 1025044; 1025045; 1025046; 1025047; 1025048
Data collection: CrystalPlan (Zikovsky, J. et al. 2011) for Rubrene_neutron, BIPa_neutron_100K; CrysAlis PRO, Agilent Technologies Version 1.171.36.28 for Rubrene_Xray_multipolemodel; CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for BIPa_X_multipole_model, BIPa_X_MM_Shade. Cell refinement: MANTID (Taylor, J. et al. 2012) for Rubrene_neutron, BIPa_neutron_100K; CrysAlis PRO, Agilent Technologies Version 1.171.36.28 for Rubrene_Xray_multipolemodel; CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for BIPa_X_multipole_model, BIPa_X_MM_Shade. Data reduction: MANTID (Taylor, J. et al. 2012) & ANVRED2X (local program) for Rubrene_neutron, BIPa_neutron_100K; CrysAlis PRO, Agilent Technologies Version 1.171.36.28 for Rubrene_Xray_multipolemodel; CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for BIPa_X_multipole_model, BIPa_X_MM_Shade. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for Rubrene_Xray_multipolemodel. Program(s) used to refine structure: GSAS (Larson & Von Dreele, 2004) for Rubrene_neutron, BIPa_neutron_100K; SHELXL97 (Sheldrick, 2008) for Rubrene_Xray_multipolemodel; Volkov et al., (2006) for Rubrene_Xray_IAM, Rubrene_Xray_IAM_HO, BIPa_X_multipole_model, BIPa_X_MM_Shade, BIPa_Xray_IAM, BIPa_X_HO_IAM. Molecular graphics: XD2006 (Volkov et al., 2006) for Rubrene_Xray_multipolemodel; Volkov et al., (2006) for Rubrene_Xray_IAM, Rubrene_Xray_IAM_HO, BIPa_Xray_IAM, BIPa_X_HO_IAM. Software used to prepare material for publication: XD2006 (Volkov et al., 2006) for Rubrene_Xray_multipolemodel; Volkov et al., (2006) for Rubrene_Xray_IAM, Rubrene_Xray_IAM_HO, BIPa_Xray_IAM, BIPa_X_HO_IAM.
C42H28 | F(000) = 697.76 |
Mr = 532.69 | Dx = 1.299 Mg m−3 |
Orthorhombic, Cmca | Neutron radiation, λ = 0.4-3.4 Å |
Hall symbol: -C 2bc 2 | Cell parameters from 1000 reflections |
a = 26.7972 (3) Å | µ = 0.20 mm−1 |
b = 7.1617 (1) Å | T = 100 K |
c = 14.1940 (2) Å | Block, red |
V = 2724.01 (5) Å3 | 1.50 × 1.50 × 1.00 mm |
Z = 4 |
TOPAZ Single Crystal Diffractometer | 24945 measured reflections |
Radiation source: spallation neutron source, SNS BL12 | 22955 independent reflections |
Not applicable to TOF Laue technique monochromator | 22955 reflections with > 3σ(I) |
time–of–flight Laue scans | h = −58→63 |
Absorption correction: analytical The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 1.189 + 0.789 * lambda [cm-1] The value of 1.978(cm-1)given in _exptl_absorpt_coefficient_mu is the value at 1 Å | k = −17→9 |
Tmin = 0.646, Tmax = 0.848 | l = −34→34 |
Refinement on F2 | All H-atom parameters refined |
Least-squares matrix: full | Weighting scheme based on measured s.u.'s |
R[F2 > 2σ(F2)] = 0.046 | (Δ/σ)max < 0.001 |
wR(F2) = 0.055 | Δρmax = 0.23 e Å−3 |
S = 1.57 | Δρmin = −0.31 e Å−3 |
22775 reflections | Extinction correction: B-C Secondary type 1 Lorenzian |
182 parameters | Extinction coefficient: 0.08E-05 (3) |
0 restraints |
C42H28 | V = 2724.01 (5) Å3 |
Mr = 532.69 | Z = 4 |
Orthorhombic, Cmca | Neutron radiation, λ = 0.4-3.4 Å |
a = 26.7972 (3) Å | µ = 0.20 mm−1 |
b = 7.1617 (1) Å | T = 100 K |
c = 14.1940 (2) Å | 1.50 × 1.50 × 1.00 mm |
TOPAZ Single Crystal Diffractometer | 24945 measured reflections |
Absorption correction: analytical The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 1.189 + 0.789 * lambda [cm-1] The value of 1.978(cm-1)given in _exptl_absorpt_coefficient_mu is the value at 1 Å | 22955 independent reflections |
Tmin = 0.646, Tmax = 0.848 | 22955 reflections with > 3σ(I) |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.055 | All H-atom parameters refined |
S = 1.57 | Δρmax = 0.23 e Å−3 |
22775 reflections | Δρmin = −0.31 e Å−3 |
182 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.027308 (14) | 0.0 | 0.0 | 0.00978 | |
C2 | 0.053187 (10) | −0.14434 (4) | 0.048949 (17) | 0.01041 | |
C3 | 0.026811 (10) | −0.29586 (4) | 0.087630 (17) | 0.01059 | |
C4 | 0.052041 (11) | −0.44708 (4) | 0.133976 (19) | 0.01351 | |
C5 | 0.026484 (12) | −0.58998 (4) | 0.17539 (2) | 0.0152 | |
C6 | 0.107508 (10) | −0.13462 (4) | 0.072664 (17) | 0.01121 | |
C7 | 0.142796 (11) | −0.24848 (5) | 0.02859 (2) | 0.01465 | |
C8 | 0.192043 (12) | −0.25130 (5) | 0.05955 (2) | 0.01876 | |
C9 | 0.207040 (12) | −0.13900 (5) | 0.13453 (2) | 0.0211 | |
C10 | 0.172212 (13) | −0.02479 (5) | 0.17886 (2) | 0.0203 | |
C11 | 0.122818 (12) | −0.02353 (5) | 0.148310 (19) | 0.01548 | |
H4 | 0.09247 (3) | −0.44660 (12) | 0.13632 (5) | 0.0307 | |
H5 | 0.04640 (3) | −0.70248 (12) | 0.21052 (6) | 0.03414 | |
H7 | 0.13131 (3) | −0.33549 (12) | −0.03021 (5) | 0.03286 | |
H8 | 0.21886 (3) | −0.34232 (14) | 0.02525 (7) | 0.03953 | |
H9 | 0.24554 (3) | −0.14180 (15) | 0.15836 (6) | 0.04295 | |
H10 | 0.18338 (3) | 0.06333 (15) | 0.23747 (6) | 0.04324 | |
H11 | 0.09552 (3) | 0.06350 (13) | 0.18360 (5) | 0.03518 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.00972 (14) | 0.00961 (16) | 0.01000 (12) | 0.0 | 0.0 | 0.00128 (10) |
C2 | 0.01055 (10) | 0.00988 (11) | 0.01081 (9) | 0.00085 (8) | 0.00014 (7) | 0.00104 (7) |
C3 | 0.01197 (10) | 0.00962 (11) | 0.01017 (9) | 0.00081 (8) | 0.00030 (7) | 0.00145 (7) |
C4 | 0.01527 (12) | 0.01163 (12) | 0.01362 (10) | 0.00258 (9) | 0.00125 (8) | 0.00323 (8) |
C5 | 0.01890 (13) | 0.01151 (13) | 0.01519 (11) | 0.00195 (10) | 0.00095 (9) | 0.00431 (9) |
C6 | 0.01057 (10) | 0.01180 (12) | 0.01127 (9) | 0.00134 (8) | −0.00027 (7) | 0.00068 (8) |
C7 | 0.01196 (11) | 0.01435 (14) | 0.01764 (11) | 0.00161 (9) | 0.00217 (9) | −0.00129 (9) |
C8 | 0.01101 (12) | 0.02017 (16) | 0.02509 (14) | 0.00269 (10) | 0.00259 (10) | 0.00194 (11) |
C9 | 0.01212 (13) | 0.02789 (19) | 0.02328 (13) | −0.00009 (11) | −0.00322 (10) | 0.00430 (12) |
C10 | 0.01691 (14) | 0.02736 (19) | 0.01664 (11) | −0.00163 (12) | −0.00526 (10) | −0.00124 (11) |
C11 | 0.01433 (13) | 0.01907 (15) | 0.01303 (10) | 0.00120 (10) | −0.00179 (9) | −0.00265 (9) |
H4 | 0.0205 (3) | 0.0317 (4) | 0.0400 (3) | 0.0049 (3) | 0.0018 (3) | 0.0113 (3) |
H5 | 0.0346 (4) | 0.0264 (4) | 0.0415 (4) | 0.0077 (3) | 0.0003 (3) | 0.0152 (3) |
H7 | 0.0301 (4) | 0.0336 (4) | 0.0349 (3) | 0.0016 (3) | 0.0010 (3) | −0.0146 (3) |
H8 | 0.0239 (4) | 0.0387 (5) | 0.0560 (5) | 0.0087 (3) | 0.0080 (3) | −0.0074 (4) |
H9 | 0.0201 (4) | 0.0592 (6) | 0.0495 (5) | 0.0011 (3) | −0.0097 (3) | 0.0017 (4) |
H10 | 0.0379 (5) | 0.0575 (6) | 0.0343 (4) | −0.0046 (4) | −0.0126 (3) | −0.0157 (4) |
H11 | 0.0297 (4) | 0.0417 (5) | 0.0342 (3) | 0.0082 (3) | 0.0004 (3) | −0.0156 (3) |
C1—C1i | 1.4636 (8) | C6—C11 | 1.3980 (4) |
C1—C2 | 1.4256 (3) | C7—C8 | 1.3911 (4) |
C2—C3 | 1.4067 (4) | C7—H7 | 1.0862 (8) |
C2—C6 | 1.4957 (4) | C8—C9 | 1.3931 (5) |
C3—C3i | 1.4370 (5) | C8—H8 | 1.0855 (9) |
C3—C4 | 1.4362 (4) | C9—C10 | 1.3914 (5) |
C4—C5 | 1.3646 (4) | C9—H9 | 1.0858 (9) |
C4—H4 | 1.0839 (8) | C10—C11 | 1.3929 (5) |
C5—C5i | 1.4194 (6) | C10—H10 | 1.0863 (9) |
C5—H5 | 1.0875 (8) | C11—C6 | 1.3980 (4) |
C6—C7 | 1.3966 (4) | C11—H11 | 1.0837 (8) |
C1i—C1—C2 | 119.109 (17) | C7—C6—C11 | 118.53 (3) |
C2—C1—C2ii | 121.78 (3) | C6—C7—C8 | 120.62 (3) |
C1—C2—C3 | 120.34 (3) | C6—C7—H7 | 119.16 (5) |
C1—C2—C6 | 123.33 (3) | C8—C7—H7 | 120.22 (5) |
C3—C2—C6 | 115.92 (2) | C7—C8—C9 | 120.44 (3) |
C2—C3—C3i | 120.164 (15) | C7—C8—H8 | 119.67 (6) |
C2—C3—C4 | 121.60 (3) | C9—C8—H8 | 119.89 (6) |
C3i—C3—C4 | 118.084 (16) | C8—C9—C10 | 119.43 (3) |
C3—C4—C5 | 121.78 (3) | C8—C9—H9 | 120.09 (6) |
C3—C4—H4 | 118.83 (5) | C10—C9—H9 | 120.48 (6) |
C5—C4—H4 | 119.39 (5) | C9—C10—C11 | 120.03 (3) |
C4—C5—C5i | 120.126 (18) | C9—C10—H10 | 120.21 (6) |
C4—C5—H5 | 120.46 (5) | C11—C10—H10 | 119.76 (6) |
C5i—C5—H5 | 119.39 (5) | C6—C11—C10 | 120.95 (3) |
C2—C6—C7 | 122.08 (3) | C6—C11—H11 | 118.97 (5) |
C2—C6—C11 | 119.01 (2) | C10—C11—H11 | 120.08 (5) |
Symmetry codes: (i) −x, y, z; (ii) x, −y, −z. |
C42H28 | Z = 4 |
Mr = 532.69 | F(000) = 1120 |
Orthorhombic, Cmca | Dx = 1.298 Mg m−3 |
Hall symbol: -C 2bc 2 | Mo Kα radiation, λ = 0.7107 Å |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | Block, orange |
V = 2726.52 (5) Å3 | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 6070 reflections with > 3σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.3590 pixels mm-1 | θmax = 51.4°, θmin = 2.9° |
ω scans | h = 0→58 |
Absorption correction: analytical ? | k = 0→15 |
Tmin = 0.983, Tmax = 0.987 | l = 0→31 |
83536 measured reflections |
Refinement on F2 | 383 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.022 | w2 = 1/[s2(Fo2)] |
wR(F2) = 0.055 | (Δ/σ)max < 0.001 |
S = 1.49 | Δρmax = 0.18 e Å−3 |
6070 reflections | Δρmin = −0.18 e Å−3 |
C42H28 | V = 2726.52 (5) Å3 |
Mr = 532.69 | Z = 4 |
Orthorhombic, Cmca | Mo Kα radiation |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Absorption correction: analytical ? | 6070 reflections with > 3σ(I) |
Tmin = 0.983, Tmax = 0.987 | Rint = 0.033 |
83536 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | 383 parameters |
wR(F2) = 0.055 | 0 restraints |
S = 1.49 | Δρmax = 0.18 e Å−3 |
6070 reflections | Δρmin = −0.18 e Å−3 |
Experimental. A nitrogen gas-flow low temperature device was used for cooling. A face indexed analytical absorption correction was performed. |
x | y | z | Uiso*/Ueq | ||
C(1) | 0.027310 (9) | 0 | 0 | 0.01 | |
C(2) | 0.053210 (7) | −0.14439 (3) | 0.048940 (14) | 0.01 | |
C(3) | 0.026843 (7) | −0.29588 (3) | 0.087621 (14) | 0.011 | |
C(4) | 0.052113 (9) | −0.44714 (3) | 0.133971 (16) | 0.014 | |
C(5) | 0.026536 (9) | −0.59004 (3) | 0.175531 (17) | 0.015 | |
C(6) | 0.107556 (8) | −0.13457 (3) | 0.072679 (14) | 0.012 | |
C(7) | 0.142855 (8) | −0.24862 (3) | 0.028629 (18) | 0.015 | |
C(8) | 0.192099 (9) | −0.25175 (4) | 0.05959 (2) | 0.019 | |
C(9) | 0.207162 (10) | −0.13947 (5) | 0.13449 (2) | 0.021 | |
C(10) | 0.172337 (11) | −0.02459 (5) | 0.17890 (2) | 0.02 | |
C(11) | 0.122824 (9) | −0.02346 (4) | 0.148321 (17) | 0.016 | |
H(4) | 0.092764 | −0.44605 | 0.135021 | 0.028534* | |
H(5) | 0.04675 | −0.700632 | 0.211934 | 0.041594* | |
H(7) | 0.131777 | −0.334537 | −0.031174 | 0.03803* | |
H(8) | 0.218581 | −0.34321 | 0.024027 | 0.03615* | |
H(9) | 0.245874 | −0.14269 | 0.157882 | 0.033709* | |
H(10) | 0.183126 | 0.066417 | 0.236951 | 0.046305* | |
H(11) | 0.095492 | 0.065424 | 0.183249 | 0.037348* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C(1) | 0.01000 (8) | 0.00907 (8) | 0.01081 (9) | 0 | 0 | 0.00128 (7) |
C(2) | 0.01058 (6) | 0.00979 (6) | 0.01104 (7) | 0.00073 (5) | −0.00007 (5) | 0.00127 (5) |
C(3) | 0.01222 (7) | 0.00933 (7) | 0.01058 (7) | 0.00080 (5) | 0.00020 (5) | 0.00134 (5) |
C(4) | 0.01505 (8) | 0.01169 (7) | 0.01390 (8) | 0.00275 (6) | 0.00109 (6) | 0.00330 (6) |
C(5) | 0.01875 (9) | 0.01131 (8) | 0.01543 (8) | 0.00202 (6) | 0.00074 (6) | 0.00394 (6) |
C(6) | 0.01085 (7) | 0.01189 (7) | 0.01177 (7) | 0.00132 (5) | −0.00027 (5) | 0.00054 (5) |
C(7) | 0.01233 (7) | 0.01442 (8) | 0.01762 (9) | 0.00172 (6) | 0.00206 (6) | −0.00103 (7) |
C(8) | 0.01156 (8) | 0.02027 (11) | 0.02498 (11) | 0.00269 (7) | 0.00225 (7) | 0.00169 (9) |
C(9) | 0.01258 (8) | 0.02726 (13) | 0.02331 (11) | 0.00031 (8) | −0.00324 (7) | 0.00380 (10) |
C(10) | 0.01673 (9) | 0.02706 (13) | 0.01696 (10) | −0.00135 (9) | −0.00506 (7) | −0.00137 (9) |
C(11) | 0.01467 (8) | 0.01876 (9) | 0.01332 (8) | 0.00128 (7) | −0.00174 (6) | −0.00236 (7) |
C(1)—C(1)i | 1.4644 (5) | C(6)—C(7) | 1.3978 (3) |
C(1)—C(1)ii | 1.4644 (5) | C(6)—C(11) | 1.3981 (3) |
C(1)—C(2) | 1.4263 (2) | C(7)—C(8) | 1.3917 (3) |
C(1)—C(2)iii | 1.4263 (2) | C(7)—H(7) | 1.0900 (3) |
C(2)—C(3) | 1.4065 (3) | C(8)—C(9) | 1.3933 (4) |
C(2)—C(6) | 1.4972 (3) | C(8)—H(8) | 1.0900 (3) |
C(3)—C(3)i | 1.4394 (4) | C(9)—C(10) | 1.3950 (4) |
C(3)—C(4) | 1.4371 (3) | C(9)—H(9) | 1.0900 (3) |
C(4)—C(5) | 1.3658 (3) | C(10)—C(11) | 1.3967 (3) |
C(4)—H(4) | 1.0900 (2) | C(10)—H(10) | 1.0900 (3) |
C(5)—C(5)i | 1.4229 (5) | C(11)—H(11) | 1.0900 (2) |
C(5)—H(5) | 1.0900 (2) | ||
C(1)i—C(1)—C(2) | 119.135 (12) | C(2)—C(6)—C(7) | 122.05 (2) |
C(1)i—C(1)—C(2)iii | 119.135 (12) | C(2)—C(6)—C(11) | 118.992 (19) |
C(1)ii—C(1)—C(2) | 119.135 (12) | C(7)—C(6)—C(11) | 118.56 (2) |
C(1)ii—C(1)—C(2)iii | 119.135 (12) | C(6)—C(7)—C(8) | 120.68 (2) |
C(2)—C(1)—C(2)iii | 121.73 (2) | C(6)—C(7)—H(7) | 119.60 (2) |
C(1)—C(2)—C(3) | 120.312 (18) | C(8)—C(7)—H(7) | 119.71 (2) |
C(1)—C(2)—C(6) | 123.334 (19) | C(7)—C(8)—C(9) | 120.46 (3) |
C(1)iii—C(2)—C(3) | 120.312 (18) | C(7)—C(8)—H(8) | 118.76 (3) |
C(1)iii—C(2)—C(6) | 123.334 (19) | C(9)—C(8)—H(8) | 120.78 (3) |
C(3)—C(2)—C(6) | 115.937 (18) | C(8)—C(9)—C(10) | 119.44 (3) |
C(2)—C(3)—C(3)i | 120.173 (11) | C(8)—C(9)—H(9) | 119.77 (3) |
C(2)—C(3)—C(4) | 121.546 (19) | C(10)—C(9)—H(9) | 120.80 (3) |
C(3)i—C(3)—C(4) | 118.127 (12) | C(9)—C(10)—C(11) | 119.93 (3) |
C(3)—C(4)—C(5) | 121.72 (2) | C(9)—C(10)—H(10) | 121.12 (3) |
C(3)—C(4)—H(4) | 118.18 (2) | C(11)—C(10)—H(10) | 118.94 (3) |
C(5)—C(4)—H(4) | 120.10 (2) | C(6)—C(11)—C(10) | 120.92 (2) |
C(4)—C(5)—C(5)i | 120.137 (14) | C(6)—C(11)—H(11) | 119.02 (2) |
C(4)—C(5)—H(5) | 119.97 (2) | C(10)—C(11)—H(11) | 120.05 (2) |
C(5)i—C(5)—H(5) | 119.815 (13) | ||
C(1)i—C(1)—C(2)—C(3) | 7.063 (16) | C(2)—C(6)—C(7)—C(8) | −172.57 (3) |
C(1)i—C(1)—C(2)—C(6) | −165.22 (3) | C(2)—C(6)—C(7)—H(7) | 8.252 (19) |
C(1)ii—C(1)—C(2)—C(3) | 7.063 (16) | C(2)—C(6)—C(11)—C(10) | 173.55 (3) |
C(1)ii—C(1)—C(2)—C(6) | −165.22 (3) | C(2)—C(6)—C(11)—H(11) | −6.79 (2) |
C(2)iii—C(1)—C(2)—C(3) | −172.94 (3) | C(11)—C(6)—C(7)—C(8) | 0.15 (2) |
C(2)iii—C(1)—C(2)—C(6) | 14.776 (18) | C(7)—C(6)—C(11)—C(10) | 0.60 (2) |
C(1)—C(2)—C(3)—C(4) | 177.45 (3) | C(11)—C(6)—C(7)—H(7) | −179.02 (3) |
C(1)—C(2)—C(6)—C(7) | −110.10 (3) | C(7)—C(6)—C(11)—H(11) | −179.74 (3) |
C(1)—C(2)—C(6)—C(11) | 77.21 (2) | C(6)—C(7)—C(8)—C(9) | −0.71 (3) |
C(1)iii—C(2)—C(3)—C(4) | 177.45 (3) | C(6)—C(7)—C(8)—H(8) | 179.47 (4) |
C(1)iii—C(2)—C(6)—C(7) | −110.10 (3) | H(7)—C(7)—C(8)—C(9) | 178.47 (4) |
C(1)iii—C(2)—C(6)—C(11) | 77.21 (2) | H(7)—C(7)—C(8)—H(8) | −1.35 (2) |
C(6)—C(2)—C(3)—C(4) | −9.713 (19) | C(7)—C(8)—C(9)—C(10) | 0.52 (3) |
C(3)—C(2)—C(6)—C(7) | 77.30 (2) | C(7)—C(8)—C(9)—H(9) | −179.72 (5) |
C(3)—C(2)—C(6)—C(11) | −95.39 (2) | H(8)—C(8)—C(9)—C(10) | −179.67 (5) |
C(3)i—C(3)—C(2)—C(1) | −7.136 (17) | H(8)—C(8)—C(9)—H(9) | 0.09 (3) |
C(3)i—C(3)—C(2)—C(6) | 165.70 (3) | C(8)—C(9)—C(10)—C(11) | 0.23 (3) |
C(2)—C(3)—C(4)—C(5) | 176.84 (3) | C(8)—C(9)—C(10)—H(10) | −179.03 (5) |
C(2)—C(3)—C(4)—H(4) | −3.493 (19) | H(9)—C(9)—C(10)—C(11) | −179.53 (5) |
C(3)i—C(3)—C(4)—C(5) | 1.33 (2) | H(9)—C(9)—C(10)—H(10) | 1.21 (3) |
C(3)i—C(3)—C(4)—H(4) | −179.00 (3) | C(9)—C(10)—C(11)—C(6) | −0.79 (3) |
C(3)—C(4)—C(5)—H(5) | −178.19 (4) | C(9)—C(10)—C(11)—H(11) | 179.55 (4) |
H(4)—C(4)—C(5)—H(5) | 2.14 (2) | H(10)—C(10)—C(11)—C(6) | 178.48 (4) |
C(5)i—C(5)—C(4)—C(3) | −1.36 (2) | H(10)—C(10)—C(11)—H(11) | −1.18 (2) |
C(5)i—C(5)—C(4)—H(4) | 178.98 (4) |
Symmetry codes: (i) −x, y, z; (ii) −x, −y, −z; (iii) x, −y, −z. |
C42H28 | Z = 4 |
Mr = 532.64 | F(000) = 1120 |
Orthorhombic, Cmca | Dx = 1.298 Mg m−3 |
Hall symbol: -C 2bc 2 | Mo Kα radiation, λ = 0.7107 Å |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | Block, orange |
V = 2726.52 (5) Å3 | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 6070 reflections with > 3σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.3590 pixels mm-1 | θmax = 51.4°, θmin = 2.9° |
ω scans | h = 0→58 |
Absorption correction: analytical ? | k = 0→15 |
Tmin = 0.983, Tmax = 0.987 | l = 0→31 |
83536 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | The heavy atoms from the multipole refinement was used to calculate anisotropic
hydrogen thermal parameters using the SHADE2.1 server SHADE web server for estimation of hydrogen anisotropic displacement parameters. Anders Østergaard Madsen. J. Appl. Cryst. 39, 757-758 www.shade.ki.ku.dk |
R[F2 > 2σ(F2)] = 0.022 | w2 = 1/[s2(Fo2)] |
wR(F2) = 0.055 | (Δ/σ)max < 0.001 |
S = 1.49 | Δρmax = 0.18 e Å−3 |
6070 reflections | Δρmin = −0.18 e Å−3 |
383 parameters |
C42H28 | V = 2726.52 (5) Å3 |
Mr = 532.64 | Z = 4 |
Orthorhombic, Cmca | Mo Kα radiation |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Absorption correction: analytical ? | 6070 reflections with > 3σ(I) |
Tmin = 0.983, Tmax = 0.987 | Rint = 0.033 |
83536 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | 0 restraints |
wR(F2) = 0.055 | The heavy atoms from the multipole refinement was used to calculate anisotropic
hydrogen thermal parameters using the SHADE2.1 server SHADE web server for estimation of hydrogen anisotropic displacement parameters. Anders Østergaard Madsen. J. Appl. Cryst. 39, 757-758 www.shade.ki.ku.dk |
S = 1.49 | Δρmax = 0.18 e Å−3 |
6070 reflections | Δρmin = −0.18 e Å−3 |
383 parameters |
Experimental. A nitrogen gas-flow low temperature device was used for cooling. A face indexed analytical absorption correction was performed. |
Refinement. The heavy atoms from the multipole refinement was used to calculate anisotropic hydrogen thermal parameters using the SHADE2.1 server SHADE web server for estimation of hydrogen anisotropic displacement parameters. Anders Østergaard Madsen. J. Appl. Cryst. 39, 757–758 www.shade.ki.ku.dk |
x | y | z | Uiso*/Ueq | ||
C(1) | 0.027309 (10) | 0 | 0 | 0.01 | |
C(2) | 0.053210 (7) | −0.14439 (3) | 0.048944 (14) | 0.01 | |
C(3) | 0.026842 (7) | −0.29588 (3) | 0.087620 (14) | 0.011 | |
C(4) | 0.052115 (9) | −0.44715 (3) | 0.133975 (16) | 0.014 | |
C(5) | 0.026536 (9) | −0.59004 (3) | 0.175528 (17) | 0.015 | |
C(6) | 0.107557 (8) | −0.13458 (3) | 0.072680 (15) | 0.012 | |
C(7) | 0.142857 (8) | −0.24862 (3) | 0.028629 (18) | 0.015 | |
C(8) | 0.192099 (9) | −0.25175 (4) | 0.05960 (2) | 0.019 | |
C(9) | 0.207154 (10) | −0.13946 (5) | 0.13449 (2) | 0.021 | |
C(10) | 0.172329 (11) | −0.02457 (5) | 0.17890 (2) | 0.02 | |
C(11) | 0.122819 (9) | −0.02346 (4) | 0.148318 (17) | 0.016 | |
H(4) | 0.092531 | −0.447865 | 0.135765 | 0.031 | |
H(5) | 0.046637 | −0.702414 | 0.210367 | 0.034 | |
H(7) | 0.132793 | −0.335448 | −0.031135 | 0.033 | |
H(8) | 0.218456 | −0.343594 | 0.024644 | 0.04 | |
H(9) | 0.24595 | −0.138968 | 0.15642 | 0.043 | |
H(10) | 0.181134 | 0.068506 | 0.23697 | 0.031 | |
H(11) | 0.094771 | 0.063073 | 0.181715 | 0.035 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C(1) | 0.01000 (8) | 0.00908 (9) | 0.01082 (9) | 0 | 0 | 0.00129 (7) |
C(2) | 0.01059 (6) | 0.00980 (6) | 0.01105 (7) | 0.00073 (5) | −0.00006 (5) | 0.00127 (5) |
C(3) | 0.01223 (7) | 0.00932 (7) | 0.01059 (7) | 0.00080 (5) | 0.00021 (5) | 0.00134 (5) |
C(4) | 0.01506 (8) | 0.01171 (7) | 0.01389 (8) | 0.00276 (6) | 0.00110 (6) | 0.00329 (6) |
C(5) | 0.01878 (9) | 0.01133 (8) | 0.01539 (8) | 0.00202 (6) | 0.00075 (6) | 0.00393 (6) |
C(6) | 0.01087 (7) | 0.01189 (7) | 0.01177 (7) | 0.00131 (5) | −0.00026 (5) | 0.00054 (5) |
C(7) | 0.01232 (7) | 0.01444 (8) | 0.01764 (9) | 0.00171 (6) | 0.00204 (6) | −0.00101 (7) |
C(8) | 0.01158 (8) | 0.02028 (11) | 0.02499 (11) | 0.00271 (7) | 0.00227 (7) | 0.00170 (9) |
C(9) | 0.01256 (8) | 0.02727 (13) | 0.02335 (11) | 0.00031 (8) | −0.00327 (7) | 0.00381 (10) |
C(10) | 0.01675 (9) | 0.02708 (13) | 0.01697 (10) | −0.00137 (9) | −0.00508 (7) | −0.00137 (9) |
C(11) | 0.01469 (8) | 0.01875 (9) | 0.01331 (8) | 0.00127 (7) | −0.00174 (6) | −0.00236 (7) |
H(4) | 0.020528 | 0.029586 | 0.036105 | 0.003129 | −0.001335 | 0.006668 |
H(5) | 0.035014 | 0.024093 | 0.038192 | 0.006032 | −0.003162 | 0.012973 |
H(7) | 0.026733 | 0.035666 | 0.035040 | −0.000367 | 0.002014 | −0.014106 |
H(8) | 0.022902 | 0.038456 | 0.052812 | 0.008128 | 0.005226 | −0.007858 |
H(9) | 0.018521 | 0.051708 | 0.043601 | 0.002817 | −0.008475 | 0.002324 |
H(10) | 0.029899 | 0.056191 | 0.032861 | −0.002330 | −0.008727 | −0.015203 |
H(11) | 0.023989 | 0.038364 | 0.034177 | 0.004924 | −0.001371 | −0.013843 |
C(1)—C(1)i | 1.4644 (5) | C(6)—C(7) | 1.3978 (3) |
C(1)—C(1)ii | 1.4644 (5) | C(6)—C(11) | 1.3981 (3) |
C(1)—C(2) | 1.4263 (2) | C(7)—C(8) | 1.3917 (3) |
C(1)—C(2)iii | 1.4263 (2) | C(7)—H(7) | 1.0900 (3) |
C(2)—C(3) | 1.4065 (3) | C(8)—C(9) | 1.3933 (4) |
C(2)—C(6) | 1.4972 (3) | C(8)—H(8) | 1.0900 (3) |
C(3)—C(3)i | 1.4394 (4) | C(9)—C(10) | 1.3950 (4) |
C(3)—C(4) | 1.4371 (3) | C(9)—H(9) | 1.0900 (3) |
C(4)—C(5) | 1.3658 (3) | C(10)—C(11) | 1.3967 (3) |
C(4)—H(4) | 1.0900 (2) | C(10)—H(10) | 1.0900 (3) |
C(5)—C(5)i | 1.4229 (5) | C(11)—H(11) | 1.0900 (2) |
C(5)—H(5) | 1.0900 (2) | ||
C(1)i—C(1)—C(2) | 119.135 (12) | C(2)—C(6)—C(7) | 122.05 (2) |
C(1)i—C(1)—C(2)iii | 119.135 (12) | C(2)—C(6)—C(11) | 118.992 (19) |
C(1)ii—C(1)—C(2) | 119.135 (12) | C(7)—C(6)—C(11) | 118.56 (2) |
C(1)ii—C(1)—C(2)iii | 119.135 (12) | C(6)—C(7)—C(8) | 120.68 (2) |
C(2)—C(1)—C(2)iii | 121.73 (2) | C(6)—C(7)—H(7) | 119.60 (2) |
C(1)—C(2)—C(3) | 120.312 (18) | C(8)—C(7)—H(7) | 119.71 (2) |
C(1)—C(2)—C(6) | 123.334 (19) | C(7)—C(8)—C(9) | 120.46 (3) |
C(1)iii—C(2)—C(3) | 120.312 (18) | C(7)—C(8)—H(8) | 118.76 (3) |
C(1)iii—C(2)—C(6) | 123.334 (19) | C(9)—C(8)—H(8) | 120.78 (3) |
C(3)—C(2)—C(6) | 115.937 (18) | C(8)—C(9)—C(10) | 119.44 (3) |
C(2)—C(3)—C(3)i | 120.173 (11) | C(8)—C(9)—H(9) | 119.77 (3) |
C(2)—C(3)—C(4) | 121.546 (19) | C(10)—C(9)—H(9) | 120.80 (3) |
C(3)i—C(3)—C(4) | 118.127 (12) | C(9)—C(10)—C(11) | 119.93 (3) |
C(3)—C(4)—C(5) | 121.72 (2) | C(9)—C(10)—H(10) | 121.12 (3) |
C(3)—C(4)—H(4) | 118.18 (2) | C(11)—C(10)—H(10) | 118.94 (3) |
C(5)—C(4)—H(4) | 120.10 (2) | C(6)—C(11)—C(10) | 120.92 (2) |
C(4)—C(5)—C(5)i | 120.137 (14) | C(6)—C(11)—H(11) | 119.02 (2) |
C(4)—C(5)—H(5) | 119.97 (2) | C(10)—C(11)—H(11) | 120.05 (2) |
C(5)i—C(5)—H(5) | 119.815 (13) | ||
C(1)i—C(1)—C(2)—C(3) | 7.063 (16) | C(2)—C(6)—C(7)—C(8) | −172.57 (3) |
C(1)i—C(1)—C(2)—C(6) | −165.22 (3) | C(2)—C(6)—C(7)—H(7) | 8.252 (19) |
C(1)ii—C(1)—C(2)—C(3) | 7.063 (16) | C(2)—C(6)—C(11)—C(10) | 173.55 (3) |
C(1)ii—C(1)—C(2)—C(6) | −165.22 (3) | C(2)—C(6)—C(11)—H(11) | −6.79 (2) |
C(2)iii—C(1)—C(2)—C(3) | −172.94 (3) | C(11)—C(6)—C(7)—C(8) | 0.15 (2) |
C(2)iii—C(1)—C(2)—C(6) | 14.776 (18) | C(7)—C(6)—C(11)—C(10) | 0.60 (2) |
C(1)—C(2)—C(3)—C(4) | 177.45 (3) | C(11)—C(6)—C(7)—H(7) | −179.02 (3) |
C(1)—C(2)—C(6)—C(7) | −110.10 (3) | C(7)—C(6)—C(11)—H(11) | −179.74 (3) |
C(1)—C(2)—C(6)—C(11) | 77.21 (2) | C(6)—C(7)—C(8)—C(9) | −0.71 (3) |
C(1)iii—C(2)—C(3)—C(4) | 177.45 (3) | C(6)—C(7)—C(8)—H(8) | 179.47 (4) |
C(1)iii—C(2)—C(6)—C(7) | −110.10 (3) | H(7)—C(7)—C(8)—C(9) | 178.47 (4) |
C(1)iii—C(2)—C(6)—C(11) | 77.21 (2) | H(7)—C(7)—C(8)—H(8) | −1.35 (2) |
C(6)—C(2)—C(3)—C(4) | −9.713 (19) | C(7)—C(8)—C(9)—C(10) | 0.52 (3) |
C(3)—C(2)—C(6)—C(7) | 77.30 (2) | C(7)—C(8)—C(9)—H(9) | −179.72 (5) |
C(3)—C(2)—C(6)—C(11) | −95.39 (2) | H(8)—C(8)—C(9)—C(10) | −179.67 (5) |
C(3)i—C(3)—C(2)—C(1) | −7.136 (17) | H(8)—C(8)—C(9)—H(9) | 0.09 (3) |
C(3)i—C(3)—C(2)—C(6) | 165.70 (3) | C(8)—C(9)—C(10)—C(11) | 0.23 (3) |
C(2)—C(3)—C(4)—C(5) | 176.84 (3) | C(8)—C(9)—C(10)—H(10) | −179.03 (5) |
C(2)—C(3)—C(4)—H(4) | −3.493 (19) | H(9)—C(9)—C(10)—C(11) | −179.53 (5) |
C(3)i—C(3)—C(4)—C(5) | 1.33 (2) | H(9)—C(9)—C(10)—H(10) | 1.21 (3) |
C(3)i—C(3)—C(4)—H(4) | −179.00 (3) | C(9)—C(10)—C(11)—C(6) | −0.79 (3) |
C(3)—C(4)—C(5)—H(5) | −178.19 (4) | C(9)—C(10)—C(11)—H(11) | 179.55 (4) |
H(4)—C(4)—C(5)—H(5) | 2.14 (2) | H(10)—C(10)—C(11)—C(6) | 178.48 (4) |
C(5)i—C(5)—C(4)—C(3) | −1.36 (2) | H(10)—C(10)—C(11)—H(11) | −1.18 (2) |
C(5)i—C(5)—C(4)—H(4) | 178.98 (4) |
Symmetry codes: (i) −x, y, z; (ii) −x, −y, −z; (iii) x, −y, −z. |
C42H28 | Z = 4 |
Mr = 532.69 | F(000) = 1120 |
Orthorhombic, Cmca | Dx = 1.298 Mg m−3 |
Hall symbol: -C 2bc 2 | Mo Kα radiation, λ = 0.7107 Å |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | Block, orange |
V = 2726.52 (5) Å3 | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 6070 reflections with > 3σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.3590 pixels mm-1 | θmax = 51.4°, θmin = 2.9° |
ω scans | h = 0→58 |
Absorption correction: analytical ? | k = 0→15 |
Tmin = 0.983, Tmax = 0.987 | l = 0→31 |
83536 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.047 | w2 = 1/[s2(Fo2)] |
wR(F2) = 0.135 | (Δ/σ)max < 0.001 |
S = 3.55 | Δρmax = 0.76 e Å−3 |
6070 reflections | Δρmin = −0.26 e Å−3 |
96 parameters |
C42H28 | V = 2726.52 (5) Å3 |
Mr = 532.69 | Z = 4 |
Orthorhombic, Cmca | Mo Kα radiation |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Absorption correction: analytical ? | 6070 reflections with > 3σ(I) |
Tmin = 0.983, Tmax = 0.987 | Rint = 0.033 |
83536 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 3.55 | Δρmax = 0.76 e Å−3 |
6070 reflections | Δρmin = −0.26 e Å−3 |
96 parameters |
Experimental. A nitrogen gas-flow low temperature device was used for cooling. A face indexed analytical absorption correction was performed. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.02728 (2) | 0 | 0 | 0.01 | |
C2 | 0.053200 (15) | −0.14436 (6) | 0.04904 (3) | 0.01 | |
C3 | 0.026877 (15) | −0.29592 (6) | 0.08760 (3) | 0.01 | |
C4 | 0.052090 (17) | −0.44731 (6) | 0.13400 (3) | 0.013 | |
C5 | 0.026493 (18) | −0.58999 (7) | 0.17554 (4) | 0.015 | |
C6 | 0.107596 (15) | −0.13457 (6) | 0.07272 (3) | 0.011 | |
C7 | 0.142874 (16) | −0.24868 (7) | 0.02855 (4) | 0.014 | |
C8 | 0.192182 (17) | −0.25141 (8) | 0.05976 (4) | 0.019 | |
C9 | 0.207010 (18) | −0.13937 (9) | 0.13455 (4) | 0.021 | |
C10 | 0.17226 (2) | −0.02475 (9) | 0.17896 (4) | 0.02 | |
C11 | 0.122828 (17) | −0.02348 (7) | 0.14825 (3) | 0.015 | |
H4 | 0.092515 | −0.446402 | 0.134891 | 0.0204 | |
H5 | 0.046689 | −0.700147 | 0.211941 | 0.034073 | |
H7 | 0.131739 | −0.334464 | −0.030921 | 0.029722 | |
H8 | 0.218572 | −0.342728 | 0.024543 | 0.023726 | |
H9 | 0.24561 | −0.142517 | 0.157626 | 0.02009 | |
H10 | 0.183187 | 0.066063 | 0.236652 | 0.037264 | |
H11 | 0.095641 | 0.06476 | 0.183028 | 0.029335 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.00965 (17) | 0.00890 (18) | 0.01039 (18) | 0 | 0 | 0.00083 (14) |
C2 | 0.01055 (13) | 0.00978 (13) | 0.01052 (13) | 0.00087 (10) | −0.00008 (10) | 0.00107 (10) |
C3 | 0.01236 (14) | 0.00912 (13) | 0.00994 (13) | 0.00090 (10) | 0.00021 (10) | 0.00096 (10) |
C4 | 0.01517 (15) | 0.01149 (15) | 0.01325 (15) | 0.00303 (12) | 0.00085 (11) | 0.00274 (12) |
C5 | 0.01880 (18) | 0.01130 (16) | 0.01484 (17) | 0.00225 (12) | 0.00060 (13) | 0.00340 (12) |
C6 | 0.01076 (13) | 0.01153 (14) | 0.01150 (14) | 0.00103 (11) | −0.00013 (10) | 0.00116 (11) |
C7 | 0.01264 (14) | 0.01359 (16) | 0.01721 (17) | 0.00177 (12) | 0.00236 (12) | −0.00047 (13) |
C8 | 0.01155 (15) | 0.0200 (2) | 0.0244 (2) | 0.00268 (14) | 0.00280 (14) | 0.00282 (17) |
C9 | 0.01217 (16) | 0.0271 (3) | 0.0234 (2) | 0.00003 (15) | −0.00289 (14) | 0.00476 (18) |
C10 | 0.01707 (18) | 0.0265 (3) | 0.01651 (19) | −0.00197 (16) | −0.00484 (14) | −0.00070 (16) |
C11 | 0.01472 (16) | 0.01828 (19) | 0.01290 (16) | 0.00095 (13) | −0.00149 (12) | −0.00177 (13) |
C(1)—C(1)i | 1.4631 (10) | C(6)—C(7) | 1.3985 (6) |
C(1)—C(1)ii | 1.4631 (10) | C(6)—C(11) | 1.3965 (7) |
C(1)—C(2) | 1.4270 (5) | C(7)—C(8) | 1.3945 (7) |
C(1)—C(2)iii | 1.4270 (5) | C(7)—H(7) | 1.0862 (5) |
C(2)—C(3) | 1.4056 (6) | C(8)—C(9) | 1.3892 (9) |
C(2)—C(6) | 1.4983 (6) | C(8)—H(8) | 1.0855 (5) |
C(3)—C(3)i | 1.4412 (8) | C(9)—C(10) | 1.3926 (8) |
C(3)—C(4) | 1.4375 (6) | C(9)—H(9) | 1.0858 (5) |
C(4)—C(5) | 1.3648 (7) | C(10)—C(11) | 1.3953 (7) |
C(4)—H(4) | 1.0839 (5) | C(10)—H(10) | 1.0863 (6) |
C(5)—C(5)i | 1.4206 (10) | C(11)—H(11) | 1.0837 (5) |
C(5)—H(5) | 1.0875 (5) | ||
C(1)i—C(1)—C(2) | 119.14 (2) | C(2)—C(6)—C(7) | 122.02 (4) |
C(1)i—C(1)—C(2)iii | 119.14 (2) | C(2)—C(6)—C(11) | 118.93 (4) |
C(1)ii—C(1)—C(2) | 119.14 (2) | C(7)—C(6)—C(11) | 118.66 (4) |
C(1)ii—C(1)—C(2)iii | 119.14 (2) | C(6)—C(7)—C(8) | 120.45 (5) |
C(2)—C(1)—C(2)iii | 121.73 (5) | C(6)—C(7)—H(7) | 119.56 (4) |
C(1)—C(2)—C(3) | 120.33 (4) | C(8)—C(7)—H(7) | 119.99 (4) |
C(1)—C(2)—C(6) | 123.34 (4) | C(7)—C(8)—C(9) | 120.42 (5) |
C(1)iii—C(2)—C(3) | 120.33 (4) | C(7)—C(8)—H(8) | 118.68 (5) |
C(1)iii—C(2)—C(6) | 123.34 (4) | C(9)—C(8)—H(8) | 120.91 (5) |
C(3)—C(2)—C(6) | 115.93 (3) | C(8)—C(9)—C(10) | 119.68 (4) |
C(2)—C(3)—C(3)i | 120.14 (2) | C(8)—C(9)—H(9) | 119.45 (5) |
C(2)—C(3)—C(4) | 121.65 (4) | C(10)—C(9)—H(9) | 120.87 (5) |
C(3)i—C(3)—C(4) | 118.05 (2) | C(9)—C(10)—C(11) | 119.85 (5) |
C(3)—C(4)—C(5) | 121.75 (4) | C(9)—C(10)—H(10) | 120.93 (5) |
C(3)—C(4)—H(4) | 118.10 (4) | C(11)—C(10)—H(10) | 119.21 (5) |
C(5)—C(4)—H(4) | 120.15 (4) | C(6)—C(11)—C(10) | 120.94 (5) |
C(4)—C(5)—C(5)i | 120.19 (3) | C(6)—C(11)—H(11) | 119.04 (4) |
C(4)—C(5)—H(5) | 119.87 (4) | C(10)—C(11)—H(11) | 120.02 (5) |
C(5)i—C(5)—H(5) | 119.86 (3) |
Symmetry codes: (i) −x, y, z; (ii) −x, −y, −z; (iii) x, −y, −z. |
C42H28 | Z = 4 |
Mr = 532.69 | F(000) = 1120 |
Orthorhombic, Cmca | Dx = 1.298 Mg m−3 |
Hall symbol: -C 2bc 2 | Mo Kα radiation, λ = 0.7107 Å |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | Block, orange |
V = 2726.52 (5) Å3 | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 6070 reflections with > 3σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.3590 pixels mm-1 | θmax = 51.4°, θmin = 2.9° |
ω scans | h = 0→58 |
Absorption correction: analytical ? | k = 0→15 |
Tmin = 0.983, Tmax = 0.987 | l = 0→31 |
83536 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.033 | w2 = 1/[s2(Fo2)] |
wR(F2) = 0.068 | (Δ/σ)max < 0.001 |
S = 1.31 | Δρmax = 0.10 e Å−3 |
3336 reflections | Δρmin = −0.11 e Å−3 |
96 parameters |
C42H28 | V = 2726.52 (5) Å3 |
Mr = 532.69 | Z = 4 |
Orthorhombic, Cmca | Mo Kα radiation |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Absorption correction: analytical ? | 6070 reflections with > 3σ(I) |
Tmin = 0.983, Tmax = 0.987 | Rint = 0.033 |
83536 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.31 | Δρmax = 0.10 e Å−3 |
3336 reflections | Δρmin = −0.11 e Å−3 |
96 parameters |
Experimental. A nitrogen gas-flow low temperature device was used for cooling. A face indexed analytical absorption correction was performed. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.027328 (13) | 0 | 0 | 0.01 | |
C2 | 0.053201 (9) | −0.14441 (4) | 0.048893 (19) | 0.011 | |
C3 | 0.026851 (10) | −0.29589 (4) | 0.087626 (19) | 0.011 | |
C4 | 0.052134 (12) | −0.44715 (5) | 0.13401 (2) | 0.014 | |
C5 | 0.026519 (14) | −0.59000 (5) | 0.17553 (2) | 0.016 | |
C6 | 0.107566 (10) | −0.13458 (4) | 0.07270 (2) | 0.012 | |
C7 | 0.142859 (12) | −0.24873 (5) | 0.02864 (3) | 0.015 | |
C8 | 0.192140 (13) | −0.25177 (7) | 0.05965 (4) | 0.019 | |
C9 | 0.207169 (15) | −0.13945 (9) | 0.13451 (4) | 0.022 | |
C10 | 0.172371 (17) | −0.02480 (8) | 0.17889 (3) | 0.021 | |
C11 | 0.122846 (13) | −0.02348 (6) | 0.14833 (2) | 0.016 | |
H4 | 0.092558 | −0.446401 | 0.134892 | 0.0204 | |
H5 | 0.046696 | −0.700185 | 0.211953 | 0.034073 | |
H7 | 0.131746 | −0.334407 | −0.030882 | 0.029722 | |
H8 | 0.218609 | −0.342854 | 0.024494 | 0.023726 | |
H9 | 0.24575 | −0.142528 | 0.15771 | 0.02009 | |
H10 | 0.183185 | 0.066048 | 0.236643 | 0.037264 | |
H11 | 0.095636 | 0.064776 | 0.183034 | 0.029335 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.01049 (10) | 0.00959 (10) | 0.01119 (10) | 0 | 0 | 0.00114 (7) |
C2 | 0.01116 (8) | 0.01034 (8) | 0.01145 (8) | 0.00077 (5) | −0.00004 (5) | 0.00119 (5) |
C3 | 0.01282 (9) | 0.00982 (8) | 0.01093 (8) | 0.00082 (5) | 0.00022 (5) | 0.00120 (5) |
C4 | 0.01567 (10) | 0.01224 (9) | 0.01433 (9) | 0.00271 (6) | 0.00107 (6) | 0.00314 (6) |
C5 | 0.01931 (12) | 0.01188 (9) | 0.01584 (10) | 0.00206 (7) | 0.00070 (7) | 0.00391 (7) |
C6 | 0.01143 (8) | 0.01235 (8) | 0.01221 (8) | 0.00131 (6) | −0.00028 (5) | 0.00067 (6) |
C7 | 0.01276 (9) | 0.01490 (10) | 0.01808 (11) | 0.00166 (7) | 0.00198 (7) | −0.00084 (7) |
C8 | 0.01218 (9) | 0.02048 (13) | 0.02547 (15) | 0.00258 (8) | 0.00223 (8) | 0.00180 (11) |
C9 | 0.01315 (10) | 0.02777 (18) | 0.02376 (15) | 0.00033 (10) | −0.00319 (9) | 0.00407 (12) |
C10 | 0.01737 (12) | 0.02763 (17) | 0.01737 (12) | −0.00134 (11) | −0.00496 (8) | −0.00131 (10) |
C11 | 0.01526 (10) | 0.01921 (12) | 0.01385 (10) | 0.00116 (8) | −0.00168 (7) | −0.00229 (7) |
C(1)—C(1)i | 1.4654 (7) | C(6)—C(7) | 1.3982 (4) |
C(1)—C(1)ii | 1.4654 (7) | C(6)—C(11) | 1.3980 (5) |
C(1)—C(2) | 1.4257 (3) | C(7)—C(8) | 1.3929 (5) |
C(1)—C(2)iii | 1.4257 (3) | C(7)—H(7) | 1.0862 (4) |
C(2)—C(3) | 1.4064 (4) | C(8)—C(9) | 1.3927 (8) |
C(2)—C(6) | 1.4979 (4) | C(8)—H(8) | 1.0855 (4) |
C(3)—C(3)i | 1.4398 (5) | C(9)—C(10) | 1.3934 (8) |
C(3)—C(4) | 1.4376 (4) | C(9)—H(9) | 1.0858 (4) |
C(4)—C(5) | 1.3658 (5) | C(10)—C(11) | 1.3970 (5) |
C(4)—H(4) | 1.0839 (3) | C(10)—H(10) | 1.0863 (5) |
C(5)—C(5)i | 1.4220 (8) | C(11)—H(11) | 1.0837 (4) |
C(5)—H(5) | 1.0875 (3) | ||
C(1)i—C(1)—C(2) | 119.114 (16) | C(2)—C(6)—C(7) | 122.01 (3) |
C(1)i—C(1)—C(2)iii | 119.114 (16) | C(2)—C(6)—C(11) | 119.03 (3) |
C(1)ii—C(1)—C(2) | 119.114 (16) | C(7)—C(6)—C(11) | 118.57 (3) |
C(1)ii—C(1)—C(2)iii | 119.114 (16) | C(6)—C(7)—C(8) | 120.63 (4) |
C(2)—C(1)—C(2)iii | 121.77 (3) | C(6)—C(7)—H(7) | 119.53 (3) |
C(1)—C(2)—C(3) | 120.36 (2) | C(8)—C(7)—H(7) | 119.83 (3) |
C(1)—C(2)—C(6) | 123.32 (3) | C(7)—C(8)—C(9) | 120.45 (4) |
C(1)iii—C(2)—C(3) | 120.36 (2) | C(7)—C(8)—H(8) | 118.95 (4) |
C(1)iii—C(2)—C(6) | 123.32 (3) | C(9)—C(8)—H(8) | 120.60 (4) |
C(3)—C(2)—C(6) | 115.89 (2) | C(8)—C(9)—C(10) | 119.46 (3) |
C(2)—C(3)—C(3)i | 120.152 (15) | C(8)—C(9)—H(9) | 119.71 (5) |
C(2)—C(3)—C(4) | 121.56 (2) | C(10)—C(9)—H(9) | 120.83 (5) |
C(3)i—C(3)—C(4) | 118.134 (17) | C(9)—C(10)—C(11) | 119.99 (4) |
C(3)—C(4)—C(5) | 121.67 (3) | C(9)—C(10)—H(10) | 121.04 (4) |
C(3)—C(4)—H(4) | 118.23 (3) | C(11)—C(10)—H(10) | 118.96 (5) |
C(5)—C(4)—H(4) | 120.10 (3) | C(6)—C(11)—C(10) | 120.89 (4) |
C(4)—C(5)—C(5)i | 120.186 (19) | C(6)—C(11)—H(11) | 118.95 (3) |
C(4)—C(5)—H(5) | 119.90 (3) | C(10)—C(11)—H(11) | 120.16 (4) |
C(5)i—C(5)—H(5) | 119.83 (2) |
Symmetry codes: (i) −x, y, z; (ii) −x, −y, −z; (iii) x, −y, −z. |
C42H28 | Z = 4 |
Mr = 532.69 | F(000) = 1120 |
Orthorhombic, Cmca | Dx = 1.298 Mg m−3 |
Hall symbol: -C 2bc 2 | Mo Kα radiation, λ = 0.7107 Å |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | Block, orange |
V = 2726.52 (5) Å3 | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 6070 reflections with > 3σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.3590 pixels mm-1 | θmax = 51.4°, θmin = 2.9° |
ω scans | h = 0→58 |
Absorption correction: analytical ? | k = 0→15 |
Tmin = 0.983, Tmax = 0.987 | l = 0→31 |
83536 measured reflections |
Refinement on F | 0 restraints |
Least-squares matrix: full | 4 constraints |
wR(F2) = 0.033 | All H-atom parameters refined |
S = 2.96 | w = 1/σ(F) |
6289 reflections | |
159 parameters |
C42H28 | V = 2726.52 (5) Å3 |
Mr = 532.69 | Z = 4 |
Orthorhombic, Cmca | Mo Kα radiation |
a = 26.8106 (3) Å | µ = 0.07 mm−1 |
b = 7.1602 (1) Å | T = 100 K |
c = 14.2029 (1) Å | 0.24 × 0.22 × 0.18 mm |
SuperNova, Single source at offset, Atlas diffractometer | 7703 independent reflections |
Absorption correction: analytical ? | 6070 reflections with > 3σ(I) |
Tmin = 0.983, Tmax = 0.987 | Rint = 0.033 |
83536 measured reflections |
wR(F2) = 0.033 | 159 parameters |
S = 2.96 | 0 restraints |
6289 reflections | All H-atom parameters refined |
Experimental. A nitrogen gas-flow low temperature device was used for cooling. A face indexed analytical absorption correction was performed. |
Refinement. . Hirshfeld atom refinement:. Uses aspherical atomic scattering factors obtained from Hirshfeld partitioning of a Gaussian quantum chemical wavefunction.. Hirshfeld weight functions obtained from spherically averaged unrestricted atomic densities.. Wavefunction type: rks becke88lyp using cluster charges, radius=8.0 angstrom. Gaussian basis set: cc-pVTZ. Refinement based on |F| with weight=1/σ(|F|). Negative |F|2 were pruned from the data. |F| < 4.0 σ(|F|) were pruned from the data. Eigenvalues < 0.1E-04 removed from normal equations. Reflection used in the refinement appear below. Refined using the Tonto program:. Version: 3.2 ($Rev: 4077 $). Platform: GNU-mpif90-on-LINUX. Build-date: Thu Jul 4 15:07:53 CEST 2013 |
x | y | z | Uiso*/Ueq | ||
C1 | 0.72268 (1) | 0.2500 | 0.5000 | 0.0095 | |
C2 | 0.696799 (7) | 0.10557 (3) | 0.45103 (1) | 0.0100 | |
C3 | 0.723158 (7) | −0.04588 (3) | 0.41238 (1) | 0.0102 | |
C4 | 0.642450 (7) | 0.11542 (3) | 0.42731 (1) | 0.0110 | |
C5 | 0.697892 (8) | −0.19713 (3) | 0.36602 (2) | 0.0130 | |
C6 | 0.723472 (9) | −0.34000 (3) | 0.32450 (2) | 0.0146 | |
C7 | 0.607131 (8) | 0.00143 (3) | 0.47135 (2) | 0.0143 | |
C8 | 0.557894 (9) | −0.00162 (4) | 0.44038 (2) | 0.0184 | |
C9 | 0.542865 (9) | 0.11067 (4) | 0.36546 (2) | 0.0205 | |
C10 | 0.57771 (1) | 0.22543 (4) | 0.32111 (2) | 0.0198 | |
C11 | 0.627169 (9) | 0.22650 (4) | 0.35169 (2) | 0.0151 | |
H1 | 0.6577 (2) | −0.1986 (8) | 0.3641 (4) | 0.03 | |
H2 | 0.7034 (2) | −0.4513 (8) | 0.2895 (5) | 0.04 | |
H3 | 0.6182 (2) | −0.0840 (9) | 0.5297 (4) | 0.04 | |
H4 | 0.5313 (2) | −0.0936 (9) | 0.4748 (5) | 0.04 | |
H5 | 0.5042 (2) | 0.109 (1) | 0.3420 (5) | 0.04 | |
H6 | 0.5673 (2) | 0.313 (1) | 0.2627 (5) | 0.05 | |
H7 | 0.6542 (2) | 0.3130 (9) | 0.3181 (4) | 0.04 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0096 (3) | 0.0087 (3) | 0.0101 (3) | 0.000000 (1) | 0.000000 (1) | −0.0012 (2) |
C2 | 0.0101 (2) | 0.0093 (2) | 0.0105 (2) | −0.0007 (2) | −0.0001 (2) | −0.0012 (2) |
C3 | 0.0118 (2) | 0.0088 (2) | 0.0099 (2) | −0.0008 (2) | 0.0002 (2) | −0.0013 (2) |
C4 | 0.0104 (2) | 0.0113 (2) | 0.0112 (2) | −0.0013 (2) | −0.0002 (2) | −0.0005 (2) |
C5 | 0.0146 (3) | 0.0111 (3) | 0.0133 (3) | −0.0027 (2) | 0.0010 (2) | −0.0032 (2) |
C6 | 0.0183 (3) | 0.0108 (3) | 0.0148 (3) | −0.0021 (2) | 0.0008 (2) | −0.0039 (2) |
C7 | 0.0119 (2) | 0.0139 (3) | 0.0170 (3) | −0.0017 (2) | 0.0021 (2) | 0.0010 (2) |
C8 | 0.0111 (3) | 0.0197 (4) | 0.0244 (4) | −0.0027 (2) | 0.0023 (2) | −0.0018 (3) |
C9 | 0.0120 (3) | 0.0268 (4) | 0.0228 (4) | −0.0001 (3) | −0.0033 (3) | −0.0040 (3) |
C10 | 0.0164 (3) | 0.0265 (4) | 0.0164 (3) | 0.0014 (3) | −0.0050 (3) | 0.0014 (3) |
C11 | 0.0141 (3) | 0.0183 (3) | 0.0128 (3) | −0.0013 (2) | −0.0018 (2) | 0.0024 (2) |
H1 | 0.02 (1) | 0.03 (1) | 0.04 (1) | −0.005 (8) | 0.003 (9) | −0.018 (9) |
H2 | 0.03 (1) | 0.03 (1) | 0.05 (2) | −0.01 (1) | 0.00 (1) | −0.02 (1) |
H3 | 0.03 (1) | 0.04 (1) | 0.04 (1) | 0.01 (1) | 0.01 (1) | 0.01 (1) |
H4 | 0.02 (1) | 0.05 (1) | 0.06 (2) | −0.008 (9) | 0.01 (1) | 0.01 (1) |
H5 | 0.03 (1) | 0.06 (2) | 0.04 (1) | 0.00 (1) | −0.01 (1) | 0.00 (1) |
H6 | 0.05 (1) | 0.06 (2) | 0.03 (1) | 0.02 (1) | −0.01 (1) | 0.02 (1) |
H7 | 0.02 (1) | 0.05 (1) | 0.04 (1) | −0.007 (9) | −0.004 (9) | 0.01 (1) |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | Z = 8 |
Mr = 711.51 | F(000) = 2041.53 |
Monoclinic, C2/c | Dx = 1.624 Mg m−3 |
Hall symbol: -C 2yc | Neutron radiation, λ = 0.4-3.4 Å |
a = 33.5759 (1) Å | Cell parameters from 1000 reflections |
b = 7.6607 (1) Å | µ = 0.19 mm−1 |
c = 25.1114 (2) Å | T = 100 K |
β = 114.6982 (4)° | Sphere, yellow |
V = 5868.14 (7) Å3 | 0.6 mm (radius) |
TOPAZ Single Crystal Diffractometer | 32750 measured reflections |
Radiation source: spallation neutron source, SNS BL12 | 25886 independent reflections |
Not applicable to TOF Laue technique monochromator | 25886 reflections with > 3σ(I) |
time–of–flight Laue scans | h = −65→66 |
Absorption correction: analytical The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 1.220 + 0.639 * lambda [cm-1] The value of 1.859(cm-1)given in _exptl_absorpt_coefficient_mu is the value at 1 Å | k = −15→9 |
Tmin = 0.747, Tmax = 0.888 | l = −46→50 |
Refinement on F2 | All H-atom parameters refined |
Least-squares matrix: full | Weighting scheme based on measured s.u.'s |
R[F2 > 2σ(F2)] = 0.051 | (Δ/σ)max < 0.001 |
wR(F2) = 0.040 | Δρmax = 0.21 e Å−3 |
S = 1.57 | Δρmin = −0.20 e Å−3 |
25886 reflections | Extinction correction: B-C Secondary type 1 Lorenzian |
693 parameters | Extinction coefficient: 2.71E-05 (6) |
0 restraints |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | V = 5868.14 (7) Å3 |
Mr = 711.51 | Z = 8 |
Monoclinic, C2/c | Neutron radiation, λ = 0.4-3.4 Å |
a = 33.5759 (1) Å | µ = 0.19 mm−1 |
b = 7.6607 (1) Å | T = 100 K |
c = 25.1114 (2) Å | 0.6 mm (radius) |
β = 114.6982 (4)° |
TOPAZ Single Crystal Diffractometer | 32750 measured reflections |
Absorption correction: analytical The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 1.220 + 0.639 * lambda [cm-1] The value of 1.859(cm-1)given in _exptl_absorpt_coefficient_mu is the value at 1 Å | 25886 independent reflections |
Tmin = 0.747, Tmax = 0.888 | 25886 reflections with > 3σ(I) |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.040 | All H-atom parameters refined |
S = 1.57 | Δρmax = 0.21 e Å−3 |
25886 reflections | Δρmin = −0.20 e Å−3 |
693 parameters |
x | y | z | Uiso*/Ueq | ||
O(8) | 0.39658 (3) | 0.11482 (10) | 0.21919 (4) | 0.01489 | |
O(9) | 0.45284 (3) | −0.06020 (11) | 0.23140 (4) | 0.01636 | |
N(7) | 0.405096 (16) | −0.36334 (6) | 0.23956 (2) | 0.01303 | |
C(12) | 0.41518 (2) | −0.03129 (9) | 0.22693 (3) | 0.01073 | |
C(13) | 0.38680 (2) | −0.18127 (9) | 0.23220 (3) | 0.01125 | |
C(14) | 0.44715 (2) | −0.38034 (10) | 0.29348 (3) | 0.01658 | |
C(15) | 0.37193 (3) | −0.48162 (10) | 0.24632 (4) | 0.02216 | |
C(16) | 0.41149 (4) | −0.41812 (12) | 0.18687 (4) | 0.0272 | |
N(1A) | 0.241497 (16) | 0.20861 (7) | 0.15126 (2) | 0.01394 | |
N(3A) | 0.310052 (17) | 0.13696 (7) | 0.18948 (2) | 0.01563 | |
C(2A) | 0.27790 (2) | 0.20612 (9) | 0.14256 (3) | 0.01491 | |
C(4A) | 0.29348 (3) | 0.09270 (11) | 0.22949 (3) | 0.01819 | |
C(5A) | 0.25036 (3) | 0.13835 (11) | 0.20530 (3) | 0.01731 | |
O(1A) | 0.17906 (3) | 0.34334 (11) | 0.05784 (4) | 0.01402 | |
O(2A) | 0.15295 (3) | 0.31091 (14) | 0.14433 (4) | 0.02224 | |
O(3A) | 0.08593 (3) | 0.37333 (13) | 0.12525 (4) | 0.0192 | |
O(4A) | 0.00281 (3) | 0.75773 (15) | −0.02859 (4) | 0.02577 | |
O(5A) | 0.02413 (3) | 0.81747 (13) | −0.09670 (4) | 0.02122 | |
O(6A) | 0.15061 (3) | 0.53231 (14) | −0.09893 (4) | 0.02303 | |
O(7A) | 0.20497 (3) | 0.52950 (13) | −0.01328 (4) | 0.0201 | |
N(4A) | 0.117026 (16) | 0.37149 (7) | 0.11183 (2) | 0.01329 | |
N(5A) | 0.028559 (17) | 0.74367 (7) | −0.05114 (2) | 0.0154 | |
N(6A) | 0.165867 (16) | 0.52994 (7) | −0.04511 (2) | 0.01326 | |
C(6A) | 0.14542 (2) | 0.43393 (8) | 0.03553 (3) | 0.00947 | |
C(7A) | 0.11147 (2) | 0.45055 (8) | 0.05681 (3) | 0.00993 | |
C(8A) | 0.07335 (2) | 0.54603 (9) | 0.02830 (3) | 0.01111 | |
C(9A) | 0.06685 (2) | 0.63498 (9) | −0.02272 (3) | 0.01109 | |
C(10A) | 0.09745 (2) | 0.62671 (9) | −0.04672 (3) | 0.01126 | |
C(11A) | 0.13496 (2) | 0.53180 (9) | −0.01821 (3) | 0.00999 | |
N(1B) | 0.450766 (16) | 0.28501 (6) | 0.08821 (2) | 0.01298 | |
N(3B) | 0.487819 (18) | 0.12504 (7) | 0.16323 (2) | 0.01605 | |
C(2B) | 0.44838 (2) | 0.19224 (9) | 0.13134 (3) | 0.01374 | |
C(4B) | 0.49288 (2) | 0.27731 (10) | 0.09243 (3) | 0.01525 | |
C(5B) | 0.51633 (3) | 0.17625 (10) | 0.13967 (3) | 0.01728 | |
O(1B) | 0.39643 (3) | 0.45033 (12) | −0.00902 (4) | 0.01581 | |
O(2B) | 0.36239 (3) | 0.38199 (14) | 0.06812 (4) | 0.02115 | |
O(3B) | 0.29203 (3) | 0.37336 (13) | 0.03071 (4) | 0.02185 | |
O(4B) | 0.21303 (3) | 0.81414 (13) | −0.10853 (5) | 0.0232 | |
O(5B) | 0.23647 (3) | 0.89252 (13) | −0.17290 (4) | 0.02258 | |
O(6B) | 0.37847 (3) | 0.75331 (11) | −0.15044 (4) | 0.0183 | |
O(7B) | 0.41187 (3) | 0.52577 (14) | −0.10146 (5) | 0.02462 | |
N(4B) | 0.326345 (16) | 0.42009 (6) | 0.02969 (2) | 0.01247 | |
N(5B) | 0.240795 (16) | 0.81284 (7) | −0.12813 (2) | 0.01523 | |
N(6B) | 0.382634 (16) | 0.63426 (7) | −0.11518 (2) | 0.01334 | |
C(6B) | 0.36086 (2) | 0.52453 (9) | −0.03652 (3) | 0.01047 | |
C(7B) | 0.32408 (2) | 0.52517 (8) | −0.01976 (3) | 0.01063 | |
C(8B) | 0.28552 (2) | 0.61475 (9) | −0.04893 (3) | 0.01172 | |
C(9B) | 0.28042 (2) | 0.71391 (9) | −0.09790 (3) | 0.01185 | |
C(10B) | 0.31261 (2) | 0.71734 (9) | −0.11878 (3) | 0.01209 | |
C(11B) | 0.35081 (2) | 0.62398 (9) | −0.09010 (3) | 0.01078 | |
H(131) | 0.35589 (5) | −0.1831 (2) | 0.19280 (8) | 0.03022 | |
H(132) | 0.38031 (6) | −0.1559 (2) | 0.27077 (8) | 0.02852 | |
H(141) | 0.45706 (7) | −0.5164 (2) | 0.29760 (10) | 0.04124 | |
H(142) | 0.47151 (6) | −0.2972 (3) | 0.28882 (9) | 0.03713 | |
H(143) | 0.44138 (7) | −0.3432 (3) | 0.33113 (8) | 0.03793 | |
H(151) | 0.34163 (6) | −0.4727 (3) | 0.20694 (10) | 0.04518 | |
H(152) | 0.38472 (7) | −0.6138 (2) | 0.25301 (11) | 0.04197 | |
H(153) | 0.36694 (8) | −0.4378 (3) | 0.28419 (11) | 0.04226 | |
H(161) | 0.43682 (9) | −0.3364 (3) | 0.18339 (10) | 0.0472 | |
H(162) | 0.42126 (11) | −0.5541 (3) | 0.19242 (12) | 0.05973 | |
H(163) | 0.38099 (9) | −0.4030 (4) | 0.14867 (9) | 0.05403 | |
H(3A) | 0.34349 (5) | 0.1240 (2) | 0.19690 (8) | 0.02933 | |
H(2A) | 0.28103 (7) | 0.2537 (3) | 0.10394 (9) | 0.03619 | |
H(4A) | 0.31350 (7) | 0.0322 (3) | 0.27073 (8) | 0.0422 | |
H(5A) | 0.22570 (7) | 0.1278 (3) | 0.22206 (9) | 0.04095 | |
H(8A) | 0.04924 (5) | 0.5529 (2) | 0.04668 (8) | 0.02754 | |
H(10A) | 0.09199 (6) | 0.6970 (2) | −0.08661 (7) | 0.02809 | |
H(1A) | 0.21185 (5) | 0.2595 (2) | 0.12079 (7) | 0.0273 | |
H(1B) | 0.42478 (5) | 0.3511 (2) | 0.05516 (7) | 0.02681 | |
H(3B) | 0.49483 (8) | 0.0478 (3) | 0.19933 (8) | 0.03813 | |
H(2B) | 0.41950 (6) | 0.1733 (3) | 0.13969 (9) | 0.03394 | |
H(4B) | 0.50266 (7) | 0.3461 (3) | 0.06237 (9) | 0.03777 | |
H(5B) | 0.55060 (6) | 0.1407 (3) | 0.15865 (10) | 0.04141 | |
H(8B) | 0.25948 (5) | 0.6075 (2) | −0.03405 (8) | 0.0265 | |
H(10B) | 0.30789 (6) | 0.7928 (2) | −0.15738 (8) | 0.02925 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(8) | 0.0127 (3) | 0.0111 (3) | 0.0192 (3) | −0.0005 (3) | 0.0050 (3) | 0.0005 (3) |
O(9) | 0.0104 (3) | 0.0195 (4) | 0.0204 (4) | 0.0002 (3) | 0.0076 (3) | 0.0040 (3) |
N(7) | 0.0144 (2) | 0.01136 (18) | 0.01136 (18) | 0.00137 (16) | 0.00349 (15) | −0.00007 (16) |
C(12) | 0.0092 (2) | 0.0118 (2) | 0.0103 (2) | −0.0010 (2) | 0.0033 (2) | 0.0007 (2) |
C(13) | 0.0093 (3) | 0.0113 (3) | 0.0127 (3) | −0.00009 (19) | 0.0040 (2) | 0.0013 (2) |
C(14) | 0.0136 (3) | 0.0181 (3) | 0.0153 (3) | 0.0038 (3) | 0.0033 (2) | 0.0038 (3) |
C(15) | 0.0187 (3) | 0.0138 (3) | 0.0273 (4) | −0.0033 (3) | 0.0030 (3) | 0.0048 (3) |
C(16) | 0.0445 (6) | 0.0214 (4) | 0.0166 (3) | 0.0061 (4) | 0.0136 (4) | −0.0051 (3) |
N(1A) | 0.01185 (19) | 0.0153 (2) | 0.01235 (19) | 0.00197 (16) | 0.00275 (15) | 0.00096 (16) |
N(3A) | 0.01153 (19) | 0.0160 (2) | 0.0175 (2) | 0.00161 (16) | 0.00434 (16) | −0.00093 (18) |
C(2A) | 0.0154 (3) | 0.0145 (3) | 0.0152 (3) | 0.0013 (2) | 0.0068 (2) | 0.0023 (2) |
C(4A) | 0.0155 (3) | 0.0243 (4) | 0.0113 (3) | 0.0057 (3) | 0.0022 (2) | 0.0020 (3) |
C(5A) | 0.0146 (3) | 0.0243 (3) | 0.0133 (3) | 0.0044 (3) | 0.0060 (2) | 0.0028 (3) |
O(1A) | 0.0124 (3) | 0.0175 (3) | 0.0121 (3) | 0.0054 (3) | 0.0050 (3) | 0.0036 (3) |
O(2A) | 0.0171 (4) | 0.0349 (5) | 0.0144 (3) | 0.0070 (4) | 0.0063 (3) | 0.0114 (4) |
O(3A) | 0.0204 (4) | 0.0244 (4) | 0.0180 (4) | 0.0029 (3) | 0.0132 (3) | 0.0073 (3) |
O(4A) | 0.0161 (4) | 0.0377 (5) | 0.0236 (4) | 0.0131 (4) | 0.0084 (3) | 0.0040 (4) |
O(5A) | 0.0185 (4) | 0.0228 (4) | 0.0169 (4) | 0.0084 (3) | 0.0021 (3) | 0.0071 (3) |
O(6A) | 0.0221 (4) | 0.0380 (5) | 0.0126 (3) | −0.0045 (4) | 0.0108 (3) | −0.0014 (4) |
O(7A) | 0.0121 (3) | 0.0307 (4) | 0.0197 (4) | 0.0027 (3) | 0.0089 (3) | 0.0051 (4) |
N(4A) | 0.0145 (2) | 0.01537 (19) | 0.01119 (18) | 0.00113 (17) | 0.00655 (15) | 0.00318 (16) |
N(5A) | 0.01136 (19) | 0.0169 (2) | 0.0142 (2) | 0.00415 (16) | 0.00153 (16) | 0.00013 (17) |
N(6A) | 0.0134 (2) | 0.0164 (2) | 0.01228 (18) | −0.00020 (16) | 0.00764 (16) | 0.00050 (16) |
C(6A) | 0.0090 (2) | 0.0110 (2) | 0.0083 (2) | 0.00128 (19) | 0.00339 (19) | 0.00058 (19) |
C(7A) | 0.0099 (2) | 0.0109 (2) | 0.0092 (2) | 0.00084 (19) | 0.0042 (2) | 0.0015 (2) |
C(8A) | 0.0094 (3) | 0.0129 (3) | 0.0110 (3) | 0.0010 (2) | 0.0043 (2) | 0.0007 (2) |
C(9A) | 0.0096 (2) | 0.0121 (2) | 0.0104 (2) | 0.0018 (2) | 0.0030 (2) | 0.0010 (2) |
C(10A) | 0.0111 (3) | 0.0125 (3) | 0.0092 (2) | 0.0010 (2) | 0.0032 (2) | 0.0019 (2) |
C(11A) | 0.0100 (2) | 0.0115 (2) | 0.0086 (2) | 0.0007 (2) | 0.00415 (19) | 0.0010 (2) |
N(1B) | 0.01211 (19) | 0.01323 (19) | 0.01258 (19) | 0.00122 (15) | 0.00415 (15) | 0.00189 (16) |
N(3B) | 0.0198 (2) | 0.0151 (2) | 0.01242 (19) | 0.00336 (18) | 0.00597 (17) | 0.00289 (17) |
C(2B) | 0.0148 (3) | 0.0132 (3) | 0.0154 (3) | −0.0002 (2) | 0.0084 (2) | 0.0005 (2) |
C(4B) | 0.0151 (3) | 0.0173 (3) | 0.0159 (3) | 0.0013 (2) | 0.0090 (2) | 0.0024 (3) |
C(5B) | 0.0124 (3) | 0.0207 (3) | 0.0176 (3) | 0.0045 (2) | 0.0051 (2) | 0.0016 (3) |
O(1B) | 0.0108 (3) | 0.0217 (4) | 0.0154 (3) | 0.0047 (3) | 0.0060 (3) | 0.0063 (3) |
O(2B) | 0.0149 (4) | 0.0343 (5) | 0.0127 (3) | 0.0024 (3) | 0.0043 (3) | 0.0068 (3) |
O(3B) | 0.0169 (4) | 0.0278 (4) | 0.0246 (4) | 0.0026 (3) | 0.0124 (3) | 0.0120 (4) |
O(4B) | 0.0131 (4) | 0.0274 (4) | 0.0295 (5) | 0.0074 (3) | 0.0093 (3) | 0.0086 (4) |
O(5B) | 0.0210 (4) | 0.0241 (4) | 0.0204 (4) | 0.0086 (3) | 0.0065 (3) | 0.0086 (4) |
O(6B) | 0.0235 (4) | 0.0179 (4) | 0.0191 (4) | −0.0001 (3) | 0.0145 (3) | 0.0030 (3) |
O(7B) | 0.0222 (4) | 0.0322 (5) | 0.0270 (4) | 0.0112 (4) | 0.0177 (4) | 0.0095 (4) |
N(4B) | 0.01291 (19) | 0.01375 (19) | 0.01202 (18) | 0.00136 (15) | 0.00647 (16) | 0.00173 (16) |
N(5B) | 0.0114 (2) | 0.0142 (2) | 0.0176 (2) | 0.00285 (16) | 0.00364 (17) | 0.00243 (17) |
N(6B) | 0.01333 (19) | 0.0158 (2) | 0.01299 (18) | −0.00068 (17) | 0.00753 (16) | −0.00028 (17) |
C(6B) | 0.0089 (2) | 0.0115 (2) | 0.0113 (3) | 0.0006 (2) | 0.0045 (2) | 0.0008 (2) |
C(7B) | 0.0099 (2) | 0.0108 (2) | 0.0117 (3) | 0.0006 (2) | 0.0050 (2) | 0.0007 (2) |
C(8B) | 0.0099 (3) | 0.0115 (3) | 0.0143 (3) | 0.0009 (2) | 0.0056 (2) | 0.0013 (2) |
C(9B) | 0.0098 (3) | 0.0113 (3) | 0.0139 (3) | 0.0009 (2) | 0.0043 (2) | 0.0010 (2) |
C(10B) | 0.0118 (3) | 0.0121 (3) | 0.0120 (3) | 0.0005 (2) | 0.0046 (2) | 0.0015 (2) |
C(11B) | 0.0100 (2) | 0.0115 (2) | 0.0115 (2) | 0.0003 (2) | 0.0051 (2) | 0.0005 (2) |
H(131) | 0.0187 (7) | 0.0274 (7) | 0.0314 (8) | −0.0018 (6) | −0.0025 (6) | 0.0052 (6) |
H(132) | 0.0383 (9) | 0.0253 (7) | 0.0328 (8) | 0.0021 (6) | 0.0255 (7) | 0.0014 (6) |
H(141) | 0.0376 (10) | 0.0271 (8) | 0.0488 (12) | 0.0147 (8) | 0.0080 (9) | 0.0094 (8) |
H(142) | 0.0211 (8) | 0.0437 (10) | 0.0420 (10) | −0.0044 (7) | 0.0087 (7) | 0.0090 (9) |
H(143) | 0.0362 (10) | 0.0566 (12) | 0.0184 (7) | 0.0048 (9) | 0.0088 (7) | −0.0006 (8) |
H(151) | 0.0267 (9) | 0.0362 (9) | 0.0503 (12) | −0.0085 (8) | −0.0060 (8) | 0.0095 (9) |
H(152) | 0.0388 (10) | 0.0185 (7) | 0.0583 (13) | −0.0004 (7) | 0.0102 (9) | 0.0059 (8) |
H(153) | 0.0454 (12) | 0.0399 (10) | 0.0499 (12) | −0.0070 (9) | 0.0283 (10) | 0.0074 (9) |
H(161) | 0.0622 (15) | 0.0510 (12) | 0.0438 (12) | 0.0040 (11) | 0.0375 (11) | −0.0011 (10) |
H(162) | 0.105 (2) | 0.0301 (10) | 0.0536 (14) | 0.0202 (12) | 0.0427 (15) | −0.0056 (10) |
H(163) | 0.0682 (16) | 0.0588 (14) | 0.0220 (8) | −0.0002 (12) | 0.0058 (9) | −0.0082 (9) |
H(3A) | 0.0200 (7) | 0.0287 (7) | 0.0389 (9) | 0.0015 (6) | 0.0119 (6) | 0.0002 (7) |
H(2A) | 0.0404 (10) | 0.0430 (10) | 0.0319 (9) | 0.0044 (8) | 0.0217 (8) | 0.0133 (8) |
H(4A) | 0.0360 (10) | 0.0623 (13) | 0.0206 (8) | 0.0179 (9) | 0.0042 (7) | 0.0140 (8) |
H(5A) | 0.0335 (10) | 0.0622 (13) | 0.0359 (9) | 0.0076 (9) | 0.0232 (8) | 0.0077 (10) |
H(8A) | 0.0228 (7) | 0.0364 (8) | 0.0292 (8) | 0.0040 (6) | 0.0166 (6) | 0.0035 (7) |
H(10A) | 0.0321 (8) | 0.0326 (8) | 0.0195 (6) | 0.0053 (7) | 0.0108 (6) | 0.0111 (6) |
H(1A) | 0.0213 (7) | 0.0290 (7) | 0.0259 (7) | 0.0048 (6) | 0.0042 (6) | 0.0035 (6) |
H(1B) | 0.0221 (7) | 0.0275 (7) | 0.0247 (7) | 0.0057 (6) | 0.0037 (6) | 0.0058 (6) |
H(3B) | 0.0589 (13) | 0.0306 (9) | 0.0245 (8) | 0.0096 (8) | 0.0170 (8) | 0.0103 (7) |
H(2B) | 0.0296 (9) | 0.0374 (9) | 0.0453 (10) | −0.0027 (7) | 0.0259 (8) | 0.0027 (8) |
H(4B) | 0.0410 (10) | 0.0422 (10) | 0.0423 (10) | 0.0033 (8) | 0.0294 (9) | 0.0154 (9) |
H(5B) | 0.0218 (8) | 0.0511 (11) | 0.0468 (11) | 0.0123 (8) | 0.0098 (8) | 0.0088 (10) |
H(8B) | 0.0223 (7) | 0.0311 (8) | 0.0324 (8) | 0.0037 (6) | 0.0177 (6) | 0.0055 (7) |
H(10B) | 0.0307 (8) | 0.0330 (8) | 0.0260 (7) | 0.0051 (7) | 0.0138 (6) | 0.0124 (7) |
O(8)—C(12) | 1.2567 (10) | C(4B)—H(4B) | 1.0782 (18) |
O(8)—H(3A) | 1.6315 (18) | C(5B)—N(3B) | 1.3762 (9) |
O(9)—C(12) | 1.2417 (10) | C(5B)—C(4B) | 1.3587 (11) |
N(7)—C(13) | 1.5040 (8) | C(5B)—H(5B) | 1.080 (2) |
N(7)—C(14) | 1.4988 (9) | O(1B)—C(6B) | 1.2397 (10) |
N(7)—C(15) | 1.4993 (10) | O(1B)—H(1B) | 1.6731 (18) |
N(7)—C(16) | 1.4865 (10) | O(2B)—N(4B) | 1.2269 (10) |
C(12)—O(8) | 1.2567 (10) | O(3B)—N(4B) | 1.2171 (10) |
C(12)—O(9) | 1.2417 (10) | O(4B)—N(5B) | 1.2226 (11) |
C(12)—C(13) | 1.5333 (9) | O(5B)—N(5B) | 1.2334 (11) |
C(13)—N(7) | 1.5040 (8) | O(6B)—N(6B) | 1.2378 (10) |
C(13)—C(12) | 1.5333 (9) | O(7B)—N(6B) | 1.2208 (10) |
C(13)—H(131) | 1.0947 (17) | N(4B)—O(2B) | 1.2269 (10) |
C(13)—H(132) | 1.0953 (17) | N(4B)—O(3B) | 1.2171 (10) |
C(14)—N(7) | 1.4988 (9) | N(4B)—C(7B) | 1.4550 (8) |
C(14)—H(141) | 1.0860 (19) | N(5B)—O(4B) | 1.2226 (11) |
C(14)—H(142) | 1.081 (2) | N(5B)—O(5B) | 1.2334 (11) |
C(14)—H(143) | 1.080 (2) | N(5B)—C(9B) | 1.4410 (8) |
C(15)—N(7) | 1.4993 (10) | N(6B)—O(6B) | 1.2378 (10) |
C(15)—H(151) | 1.085 (2) | N(6B)—O(7B) | 1.2208 (10) |
C(15)—H(152) | 1.085 (2) | N(6B)—C(11B) | 1.4516 (8) |
C(15)—H(153) | 1.085 (3) | C(6B)—O(1B) | 1.2397 (10) |
C(16)—N(7) | 1.4865 (10) | C(6B)—C(7B) | 1.4617 (9) |
C(16)—H(161) | 1.089 (3) | C(6B)—C(11B) | 1.4578 (9) |
C(16)—H(162) | 1.084 (2) | C(7B)—N(4B) | 1.4550 (8) |
C(16)—H(163) | 1.078 (3) | C(7B)—C(6B) | 1.4617 (9) |
N(1A)—C(2A) | 1.3285 (9) | C(7B)—C(8B) | 1.3752 (9) |
N(1A)—C(5A) | 1.3721 (9) | C(8B)—C(7B) | 1.3752 (9) |
N(1A)—H(1A) | 1.0449 (17) | C(8B)—C(9B) | 1.3938 (10) |
N(3A)—C(2A) | 1.3310 (9) | C(8B)—H(8B) | 1.0863 (16) |
N(3A)—C(4A) | 1.3788 (9) | C(9B)—N(5B) | 1.4410 (8) |
N(3A)—H(3A) | 1.0631 (17) | C(9B)—C(8B) | 1.3938 (10) |
C(2A)—N(1A) | 1.3285 (9) | C(9B)—C(10B) | 1.3848 (10) |
C(2A)—N(3A) | 1.3310 (9) | C(10B)—C(9B) | 1.3848 (10) |
C(2A)—H(2A) | 1.0816 (19) | C(10B)—C(11B) | 1.3796 (9) |
C(4A)—N(3A) | 1.3788 (9) | C(10B)—H(10B) | 1.0817 (17) |
C(4A)—C(5A) | 1.3612 (10) | C(11B)—N(6B) | 1.4516 (8) |
C(4A)—H(4A) | 1.0758 (19) | C(11B)—C(6B) | 1.4578 (9) |
C(5A)—N(1A) | 1.3721 (9) | C(11B)—C(10B) | 1.3796 (9) |
C(5A)—C(4A) | 1.3612 (10) | H(131)—C(13) | 1.0947 (17) |
C(5A)—H(5A) | 1.077 (2) | H(131)—H(132) | 1.791 (3) |
O(1A)—C(6A) | 1.2420 (10) | H(132)—C(13) | 1.0953 (17) |
O(1A)—H(1A) | 1.6337 (18) | H(132)—H(131) | 1.791 (3) |
O(2A)—N(4A) | 1.2303 (10) | H(141)—C(14) | 1.0860 (19) |
O(3A)—N(4A) | 1.2239 (10) | H(141)—H(142) | 1.787 (3) |
O(4A)—N(5A) | 1.2200 (11) | H(141)—H(143) | 1.765 (3) |
O(5A)—N(5A) | 1.2282 (11) | H(142)—C(14) | 1.081 (2) |
O(6A)—N(6A) | 1.2289 (10) | H(142)—H(141) | 1.787 (3) |
O(7A)—N(6A) | 1.2189 (10) | H(142)—H(143) | 1.782 (3) |
N(4A)—O(2A) | 1.2303 (10) | H(143)—C(14) | 1.080 (2) |
N(4A)—O(3A) | 1.2239 (10) | H(143)—H(141) | 1.765 (3) |
N(4A)—C(7A) | 1.4474 (8) | H(143)—H(142) | 1.782 (3) |
N(5A)—O(4A) | 1.2200 (11) | H(151)—C(15) | 1.085 (2) |
N(5A)—O(5A) | 1.2282 (11) | H(151)—H(152) | 1.789 (3) |
N(5A)—C(9A) | 1.4453 (8) | H(151)—H(153) | 1.783 (3) |
N(6A)—O(6A) | 1.2289 (10) | H(152)—C(15) | 1.085 (2) |
N(6A)—O(7A) | 1.2189 (10) | H(152)—H(151) | 1.789 (3) |
N(6A)—C(11A) | 1.4557 (8) | H(152)—H(153) | 1.782 (3) |
C(6A)—O(1A) | 1.2420 (10) | H(153)—C(15) | 1.085 (3) |
C(6A)—C(7A) | 1.4526 (9) | H(153)—H(151) | 1.783 (3) |
C(6A)—C(11A) | 1.4528 (9) | H(153)—H(152) | 1.782 (3) |
C(7A)—N(4A) | 1.4474 (8) | H(161)—C(16) | 1.089 (3) |
C(7A)—C(6A) | 1.4526 (9) | H(161)—H(162) | 1.790 (4) |
C(7A)—C(8A) | 1.3856 (9) | H(161)—H(163) | 1.780 (4) |
C(8A)—C(7A) | 1.3856 (9) | H(162)—C(16) | 1.084 (2) |
C(8A)—C(9A) | 1.3856 (9) | H(162)—H(161) | 1.790 (4) |
C(8A)—H(8A) | 1.0880 (17) | H(162)—H(163) | 1.770 (4) |
C(9A)—N(5A) | 1.4453 (8) | H(163)—C(16) | 1.078 (3) |
C(9A)—C(8A) | 1.3856 (9) | H(163)—H(161) | 1.780 (4) |
C(9A)—C(10A) | 1.3928 (9) | H(163)—H(162) | 1.770 (4) |
C(10A)—C(9A) | 1.3928 (9) | H(3A)—O(8) | 1.6315 (18) |
C(10A)—C(11A) | 1.3689 (9) | H(3A)—N(3A) | 1.0631 (17) |
C(10A)—H(10A) | 1.0832 (17) | H(2A)—C(2A) | 1.0816 (19) |
C(11A)—N(6A) | 1.4557 (8) | H(4A)—C(4A) | 1.0758 (19) |
C(11A)—C(6A) | 1.4528 (9) | H(5A)—C(5A) | 1.077 (2) |
C(11A)—C(10A) | 1.3689 (9) | H(8A)—C(8A) | 1.0880 (17) |
N(1B)—C(2B) | 1.3256 (9) | H(10A)—C(10A) | 1.0832 (17) |
N(1B)—C(4B) | 1.3742 (9) | H(1A)—N(1A) | 1.0449 (17) |
N(1B)—H(1B) | 1.0494 (16) | H(1A)—O(1A) | 1.6337 (18) |
N(3B)—C(2B) | 1.3319 (9) | H(1B)—N(1B) | 1.0494 (16) |
N(3B)—C(5B) | 1.3762 (9) | H(1B)—O(1B) | 1.6731 (18) |
N(3B)—H(3B) | 1.0242 (19) | H(3B)—N(3B) | 1.0242 (19) |
C(2B)—N(1B) | 1.3256 (9) | H(2B)—C(2B) | 1.0837 (18) |
C(2B)—N(3B) | 1.3319 (9) | H(4B)—C(4B) | 1.0782 (18) |
C(2B)—H(2B) | 1.0837 (18) | H(5B)—C(5B) | 1.080 (2) |
C(4B)—N(1B) | 1.3742 (9) | H(8B)—C(8B) | 1.0863 (16) |
C(4B)—C(5B) | 1.3587 (11) | H(10B)—C(10B) | 1.0817 (17) |
C(12)—O(8)—H(3A) | 119.50 (9) | C(7A)—C(6A)—C(11A) | 111.98 (5) |
C(13)—N(7)—C(14) | 111.95 (5) | N(4A)—C(7A)—C(6A) | 120.44 (5) |
C(13)—N(7)—C(15) | 106.84 (5) | N(4A)—C(7A)—C(8A) | 115.90 (5) |
C(13)—N(7)—C(16) | 110.85 (5) | C(6A)—C(7A)—C(8A) | 123.61 (6) |
C(14)—N(7)—C(15) | 108.00 (5) | C(7A)—C(8A)—C(9A) | 119.47 (6) |
C(14)—N(7)—C(16) | 110.35 (6) | C(7A)—C(8A)—H(8A) | 119.80 (11) |
C(15)—N(7)—C(16) | 108.69 (6) | C(9A)—C(8A)—H(8A) | 120.71 (11) |
O(8)—C(12)—O(9) | 126.46 (7) | N(5A)—C(9A)—C(8A) | 120.25 (6) |
O(8)—C(12)—C(13) | 113.21 (6) | N(5A)—C(9A)—C(10A) | 118.51 (6) |
O(9)—C(12)—C(13) | 120.31 (7) | C(8A)—C(9A)—C(10A) | 121.20 (6) |
N(7)—C(13)—C(12) | 117.96 (5) | C(9A)—C(10A)—C(11A) | 118.80 (6) |
N(7)—C(13)—H(131) | 106.46 (11) | C(9A)—C(10A)—H(10A) | 120.47 (11) |
N(7)—C(13)—H(132) | 106.13 (10) | C(11A)—C(10A)—H(10A) | 120.71 (11) |
C(12)—C(13)—H(131) | 108.67 (11) | N(6A)—C(11A)—C(6A) | 118.92 (5) |
C(12)—C(13)—H(132) | 107.70 (10) | N(6A)—C(11A)—C(10A) | 116.17 (5) |
H(131)—C(13)—H(132) | 109.75 (16) | C(6A)—C(11A)—C(10A) | 124.91 (6) |
N(7)—C(14)—H(141) | 107.76 (13) | C(2B)—N(1B)—C(4B) | 109.00 (5) |
N(7)—C(14)—H(142) | 108.71 (12) | C(2B)—N(1B)—H(1B) | 126.21 (11) |
N(7)—C(14)—H(143) | 108.81 (12) | C(4B)—N(1B)—H(1B) | 124.77 (11) |
H(141)—C(14)—H(142) | 111.13 (18) | C(2B)—N(3B)—C(5B) | 109.08 (5) |
H(141)—C(14)—H(143) | 109.22 (18) | C(2B)—N(3B)—H(3B) | 123.96 (14) |
H(142)—C(14)—H(143) | 111.12 (19) | C(5B)—N(3B)—H(3B) | 126.95 (14) |
N(7)—C(15)—H(151) | 108.46 (14) | N(1B)—C(2B)—N(3B) | 108.30 (6) |
N(7)—C(15)—H(152) | 108.47 (13) | N(1B)—C(2B)—H(2B) | 126.45 (13) |
N(7)—C(15)—H(153) | 107.85 (13) | N(3B)—C(2B)—H(2B) | 125.25 (13) |
H(151)—C(15)—H(152) | 111.08 (18) | N(1B)—C(4B)—C(5B) | 107.11 (6) |
H(151)—C(15)—H(153) | 110.5 (2) | N(1B)—C(4B)—H(4B) | 121.98 (13) |
H(152)—C(15)—H(153) | 110.41 (19) | C(5B)—C(4B)—H(4B) | 130.89 (13) |
N(7)—C(16)—H(161) | 108.50 (13) | N(3B)—C(5B)—C(4B) | 106.51 (6) |
N(7)—C(16)—H(162) | 107.78 (15) | N(3B)—C(5B)—H(5B) | 122.85 (14) |
N(7)—C(16)—H(163) | 108.97 (17) | C(4B)—C(5B)—H(5B) | 130.61 (14) |
H(161)—C(16)—H(162) | 111.0 (2) | O(2B)—N(4B)—O(3B) | 123.02 (7) |
H(161)—C(16)—H(163) | 110.5 (2) | O(2B)—N(4B)—C(7B) | 119.05 (6) |
H(162)—C(16)—H(163) | 110.0 (2) | O(3B)—N(4B)—C(7B) | 117.93 (6) |
C(2A)—N(1A)—C(5A) | 108.83 (5) | O(4B)—N(5B)—O(5B) | 122.94 (7) |
C(2A)—N(1A)—H(1A) | 123.04 (11) | O(4B)—N(5B)—C(9B) | 118.92 (6) |
C(5A)—N(1A)—H(1A) | 128.11 (11) | O(5B)—N(5B)—C(9B) | 118.13 (6) |
C(2A)—N(3A)—C(4A) | 108.54 (6) | O(6B)—N(6B)—O(7B) | 122.73 (7) |
C(2A)—N(3A)—H(3A) | 126.79 (12) | O(6B)—N(6B)—C(11B) | 117.83 (6) |
C(4A)—N(3A)—H(3A) | 124.57 (12) | O(7B)—N(6B)—C(11B) | 119.44 (6) |
N(1A)—C(2A)—N(3A) | 108.77 (6) | O(1B)—C(6B)—C(7B) | 125.05 (7) |
N(1A)—C(2A)—H(2A) | 125.69 (13) | O(1B)—C(6B)—C(11B) | 123.45 (7) |
N(3A)—C(2A)—H(2A) | 125.53 (13) | C(7B)—C(6B)—C(11B) | 111.49 (5) |
N(3A)—C(4A)—C(5A) | 106.83 (6) | N(4B)—C(7B)—C(6B) | 119.64 (5) |
N(3A)—C(4A)—H(4A) | 121.84 (13) | N(4B)—C(7B)—C(8B) | 115.63 (5) |
C(5A)—C(4A)—H(4A) | 131.33 (14) | C(6B)—C(7B)—C(8B) | 124.68 (6) |
N(1A)—C(5A)—C(4A) | 107.02 (6) | C(7B)—C(8B)—C(9B) | 118.89 (6) |
N(1A)—C(5A)—H(5A) | 122.10 (13) | C(7B)—C(8B)—H(8B) | 120.34 (11) |
C(4A)—C(5A)—H(5A) | 130.87 (13) | C(9B)—C(8B)—H(8B) | 120.76 (11) |
C(6A)—O(1A)—H(1A) | 140.75 (9) | N(5B)—C(9B)—C(8B) | 119.83 (6) |
O(2A)—N(4A)—O(3A) | 122.30 (7) | N(5B)—C(9B)—C(10B) | 119.05 (6) |
O(2A)—N(4A)—C(7A) | 119.38 (6) | C(8B)—C(9B)—C(10B) | 121.12 (6) |
O(3A)—N(4A)—C(7A) | 118.27 (6) | C(9B)—C(10B)—C(11B) | 119.67 (6) |
O(4A)—N(5A)—O(5A) | 123.93 (8) | C(9B)—C(10B)—H(10B) | 120.27 (11) |
O(4A)—N(5A)—C(9A) | 118.58 (7) | C(11B)—C(10B)—H(10B) | 120.06 (11) |
O(5A)—N(5A)—C(9A) | 117.49 (6) | N(6B)—C(11B)—C(6B) | 120.03 (5) |
O(6A)—N(6A)—O(7A) | 124.14 (7) | N(6B)—C(11B)—C(10B) | 115.95 (6) |
O(6A)—N(6A)—C(11A) | 117.36 (6) | C(6B)—C(11B)—C(10B) | 123.98 (6) |
O(7A)—N(6A)—C(11A) | 118.49 (6) | O(8)—H(3A)—N(3A) | 170.58 (18) |
O(1A)—C(6A)—C(7A) | 126.05 (6) | N(1A)—H(1A)—O(1A) | 154.94 (16) |
O(1A)—C(6A)—C(11A) | 121.92 (6) |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | F(000) = 2944 |
Mr = 711.51 | Dx = 1.62 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -C 2yc | Cell parameters from 37970 reflections |
a = 33.5939 (5) Å | θ = 2.8–57.9° |
b = 7.66580 (8) Å | µ = 0.14 mm−1 |
c = 25.1324 (3) Å | T = 100 K |
β = 114.7162 (17)° | Block, yellow |
V = 5879.29 (13) Å3 | 0.29 × 0.21 × 0.16 mm |
Z = 8 |
SuperNova, Single source at offset, Atlas diffractometer | 27262 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 21277 reflections with > 3σ(I) |
Mirror monochromator | Rint = 0.035 |
Detector resolution: 10.3590 pixels mm-1 | θmax = 58.6°, θmin = 2.4° |
ω scans | h = −73→79 |
Absorption correction: gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | k = −17→18 |
Tmin = 0.974, Tmax = 0.982 | l = −60→60 |
165808 measured reflections |
Refinement on F2 | 1306 parameters |
Least-squares matrix: full | 1 restraint |
R[F2 > 2σ(F2)] = 0.03 | w2 = 1/[s2(Fo2)] |
wR(F2) = 0.072 | (Δ/σ)max = 0.009 |
S = 0.87 | Δρmax = 0.31 e Å−3 |
21277 reflections | Δρmin = −0.26 e Å−3 |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | V = 5879.29 (13) Å3 |
Mr = 711.51 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 33.5939 (5) Å | µ = 0.14 mm−1 |
b = 7.66580 (8) Å | T = 100 K |
c = 25.1324 (3) Å | 0.29 × 0.21 × 0.16 mm |
β = 114.7162 (17)° |
SuperNova, Single source at offset, Atlas diffractometer | 27262 independent reflections |
Absorption correction: gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | 21277 reflections with > 3σ(I) |
Tmin = 0.974, Tmax = 0.982 | Rint = 0.035 |
165808 measured reflections |
R[F2 > 2σ(F2)] = 0.03 | 1306 parameters |
wR(F2) = 0.072 | 1 restraint |
S = 0.87 | Δρmax = 0.31 e Å−3 |
21277 reflections | Δρmin = −0.26 e Å−3 |
Refinement. Charge density modeled in XD2006 using the Hansen-Coppens multipole model. |
x | y | z | Uiso*/Ueq | ||
O(8) | 0.39666 (2) | 0.11489 (8) | 0.21921 (3) | 0.015 | |
O(9) | 0.45299 (2) | −0.06032 (9) | 0.23164 (3) | 0.016 | |
N(7) | 0.405081 (15) | −0.36330 (5) | 0.239618 (17) | 0.013 | |
C(12) | 0.415166 (14) | −0.03155 (5) | 0.226991 (16) | 0.011 | |
C(13) | 0.386792 (14) | −0.18131 (5) | 0.232177 (18) | 0.011 | |
C(14) | 0.447127 (16) | −0.38055 (6) | 0.29350 (2) | 0.017 | |
C(15) | 0.371814 (19) | −0.48157 (7) | 0.24655 (3) | 0.022 | |
C(16) | 0.41140 (3) | −0.41827 (8) | 0.18684 (3) | 0.027 | |
N(1A) | 0.241477 (15) | 0.20841 (5) | 0.151236 (18) | 0.014 | |
N(3A) | 0.310061 (16) | 0.13679 (6) | 0.18950 (2) | 0.015 | |
C(2A) | 0.277876 (17) | 0.20612 (6) | 0.14255 (2) | 0.015 | |
C(4A) | 0.293445 (18) | 0.09250 (7) | 0.22950 (2) | 0.018 | |
C(5A) | 0.250264 (18) | 0.13797 (7) | 0.20529 (2) | 0.017 | |
O(1A) | 0.17910 (2) | 0.34337 (8) | 0.05774 (3) | 0.014 | |
O(2A) | 0.15299 (3) | 0.31133 (13) | 0.14452 (3) | 0.022 | |
O(3A) | 0.08584 (3) | 0.37305 (11) | 0.12522 (3) | 0.019 | |
O(4A) | 0.00250 (3) | 0.75749 (16) | −0.02871 (4) | 0.026 | |
O(5A) | 0.02422 (3) | 0.81835 (11) | −0.09687 (3) | 0.021 | |
O(6A) | 0.15056 (3) | 0.53195 (14) | −0.09916 (3) | 0.023 | |
O(7A) | 0.20503 (3) | 0.52988 (12) | −0.01320 (4) | 0.020 | |
N(4A) | 0.116993 (15) | 0.37150 (5) | 0.111794 (17) | 0.013 | |
N(5A) | 0.028543 (15) | 0.74380 (6) | −0.051189 (18) | 0.015 | |
N(6A) | 0.165869 (15) | 0.53005 (5) | −0.045110 (17) | 0.013 | |
C(6A) | 0.145345 (13) | 0.43401 (5) | 0.035482 (15) | 0.010 | |
C(7A) | 0.111414 (14) | 0.45061 (5) | 0.056754 (16) | 0.010 | |
C(8A) | 0.073337 (14) | 0.54634 (5) | 0.028220 (17) | 0.011 | |
C(9A) | 0.066836 (14) | 0.63507 (5) | −0.022817 (17) | 0.011 | |
C(10A) | 0.097484 (15) | 0.62712 (5) | −0.046708 (17) | 0.011 | |
C(11A) | 0.134983 (14) | 0.53181 (5) | −0.018275 (16) | 0.010 | |
N(1B) | 0.450749 (15) | 0.28495 (5) | 0.088229 (17) | 0.013 | |
N(3B) | 0.487950 (18) | 0.12452 (6) | 0.163266 (18) | 0.016 | |
C(2B) | 0.448402 (17) | 0.19174 (5) | 0.131425 (19) | 0.014 | |
C(4B) | 0.492900 (17) | 0.27737 (6) | 0.09240 (2) | 0.016 | |
C(5B) | 0.516455 (17) | 0.17623 (6) | 0.13969 (2) | 0.017 | |
O(1B) | 0.39645 (2) | 0.44992 (9) | −0.00919 (3) | 0.016 | |
O(2B) | 0.36247 (3) | 0.38075 (13) | 0.06819 (3) | 0.021 | |
O(3B) | 0.29181 (3) | 0.37158 (13) | 0.03035 (4) | 0.021 | |
O(4B) | 0.21289 (3) | 0.81473 (12) | −0.10836 (5) | 0.023 | |
O(5B) | 0.23659 (3) | 0.89367 (12) | −0.17292 (4) | 0.022 | |
O(6B) | 0.37848 (3) | 0.75426 (10) | −0.15044 (3) | 0.018 | |
O(7B) | 0.41174 (4) | 0.52501 (14) | −0.10190 (4) | 0.024 | |
N(4B) | 0.326352 (15) | 0.41972 (5) | 0.029624 (17) | 0.012 | |
N(5B) | 0.240827 (15) | 0.81309 (5) | −0.12811 (2) | 0.015 | |
N(6B) | 0.382634 (15) | 0.63458 (5) | −0.115264 (17) | 0.013 | |
C(6B) | 0.360806 (14) | 0.52450 (5) | −0.036526 (16) | 0.011 | |
C(7B) | 0.324122 (14) | 0.52499 (5) | −0.019731 (17) | 0.011 | |
C(8B) | 0.285522 (14) | 0.61505 (5) | −0.048880 (18) | 0.012 | |
C(9B) | 0.280376 (14) | 0.71395 (5) | −0.097881 (18) | 0.012 | |
C(10B) | 0.312667 (15) | 0.71763 (5) | −0.118729 (17) | 0.012 | |
C(11B) | 0.350824 (14) | 0.62412 (5) | −0.090103 (17) | 0.011 | |
H(131) | 0.380636 | −0.153995 | 0.270348 | 0.015 | |
H(132) | 0.356684 | −0.182908 | 0.192543 | 0.015 | |
H(141) | 0.456538 | −0.516479 | 0.29604 | 0.026 | |
H(142) | 0.440517 | −0.340699 | 0.330363 | 0.026 | |
H(143) | 0.471759 | −0.298672 | 0.288867 | 0.026 | |
H(151) | 0.342291 | −0.477075 | 0.206174 | 0.034 | |
H(152) | 0.367604 | −0.436667 | 0.284732 | 0.034 | |
H(153) | 0.38514 | −0.612419 | 0.25253 | 0.034 | |
H(161) | 0.436461 | −0.33285 | 0.184978 | 0.041 | |
H(162) | 0.380475 | −0.399768 | 0.149176 | 0.041 | |
H(163) | 0.420708 | −0.554594 | 0.192499 | 0.041 | |
H(3A) | 0.343945 | 0.129243 | 0.19583 | 0.019 | |
H(2A) | 0.281517 | 0.24812 | 0.103681 | 0.019 | |
H(4A) | 0.313499 | 0.031255 | 0.270954 | 0.022 | |
H(5A) | 0.225583 | 0.129729 | 0.222357 | 0.021 | |
H(8A) | 0.049251 | 0.554026 | 0.046318 | 0.015 | |
H(10A) | 0.092339 | 0.699669 | −0.086027 | 0.014 | |
H(1A) | 0.210977 | 0.260899 | 0.119056 | 0.017 | |
H(1B) | 0.423828 | 0.351201 | 0.053689 | 0.016 | |
H(3B) | 0.496265 | 0.043896 | 0.201829 | 0.019 | |
H(2B) | 0.418914 | 0.173 | 0.138232 | 0.018 | |
H(4B) | 0.502179 | 0.34894 | 0.062185 | 0.019 | |
H(5B) | 0.550597 | 0.137684 | 0.158882 | 0.022 | |
H(8B) | 0.259778 | 0.60826 | −0.033679 | 0.015 | |
H(10B) | 0.307506 | 0.792185 | −0.157677 | 0.015 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(8) | 0.0129 (2) | 0.01169 (19) | 0.0195 (2) | −0.00025 (15) | 0.00521 (19) | 0.00035 (16) |
O(9) | 0.0104 (2) | 0.0190 (2) | 0.0199 (2) | −0.00040 (17) | 0.00699 (19) | 0.00325 (18) |
N(7) | 0.01440 (17) | 0.01112 (13) | 0.01074 (13) | 0.00089 (11) | 0.00322 (12) | −0.00017 (10) |
C(12) | 0.00918 (16) | 0.01218 (14) | 0.01078 (13) | −0.00069 (11) | 0.00316 (11) | 0.00043 (10) |
C(13) | 0.00973 (15) | 0.01138 (13) | 0.01236 (14) | −0.00013 (10) | 0.00364 (12) | 0.00119 (10) |
C(14) | 0.01377 (19) | 0.01818 (18) | 0.01483 (17) | 0.00377 (13) | 0.00299 (14) | 0.00375 (13) |
C(15) | 0.0184 (2) | 0.01416 (17) | 0.0266 (2) | −0.00330 (15) | 0.00300 (19) | 0.00510 (15) |
C(16) | 0.0446 (4) | 0.0214 (2) | 0.0167 (2) | 0.0055 (2) | 0.0147 (2) | −0.00432 (16) |
N(1A) | 0.01152 (16) | 0.01511 (15) | 0.01195 (14) | 0.00231 (11) | 0.00251 (12) | 0.00125 (11) |
N(3A) | 0.01155 (17) | 0.01609 (16) | 0.01694 (16) | 0.00171 (12) | 0.00411 (14) | −0.00062 (12) |
C(2A) | 0.01499 (19) | 0.01494 (16) | 0.01550 (17) | 0.00159 (13) | 0.00672 (15) | 0.00267 (12) |
C(4A) | 0.0155 (2) | 0.0242 (2) | 0.01096 (15) | 0.00532 (15) | 0.00219 (14) | 0.00177 (13) |
C(5A) | 0.0148 (2) | 0.0246 (2) | 0.01284 (16) | 0.00391 (15) | 0.00593 (15) | 0.00238 (14) |
O(1A) | 0.0123 (2) | 0.0174 (2) | 0.01168 (18) | 0.00606 (16) | 0.00419 (16) | 0.00384 (15) |
O(2A) | 0.0167 (3) | 0.0346 (3) | 0.0137 (2) | 0.0062 (3) | 0.0062 (2) | 0.0110 (2) |
O(3A) | 0.0203 (3) | 0.0235 (3) | 0.0182 (2) | 0.0035 (2) | 0.0129 (2) | 0.0075 (2) |
O(4A) | 0.0168 (3) | 0.0373 (4) | 0.0225 (3) | 0.0135 (3) | 0.0079 (3) | 0.0042 (3) |
O(5A) | 0.0191 (3) | 0.0231 (3) | 0.0167 (2) | 0.0077 (2) | 0.0024 (2) | 0.0072 (2) |
O(6A) | 0.0222 (4) | 0.0370 (4) | 0.0123 (2) | −0.0045 (3) | 0.0104 (2) | −0.0010 (2) |
O(7A) | 0.0127 (3) | 0.0304 (3) | 0.0195 (3) | 0.0023 (2) | 0.0092 (2) | 0.0047 (2) |
N(4A) | 0.01370 (17) | 0.01516 (14) | 0.01031 (13) | 0.00107 (11) | 0.00560 (12) | 0.00327 (10) |
N(5A) | 0.01181 (17) | 0.01687 (16) | 0.01262 (14) | 0.00432 (12) | 0.00162 (12) | 0.00065 (12) |
N(6A) | 0.01352 (17) | 0.01585 (15) | 0.01157 (14) | 0.00015 (11) | 0.00725 (12) | 0.00055 (10) |
C(6A) | 0.00984 (15) | 0.01069 (13) | 0.00839 (12) | 0.00124 (10) | 0.00340 (11) | 0.00084 (9) |
C(7A) | 0.00985 (15) | 0.01173 (13) | 0.00892 (12) | 0.00074 (10) | 0.00402 (11) | 0.00141 (9) |
C(8A) | 0.00970 (16) | 0.01370 (14) | 0.01061 (13) | 0.00097 (11) | 0.00433 (12) | 0.00097 (10) |
C(9A) | 0.00996 (16) | 0.01264 (14) | 0.00973 (13) | 0.00178 (11) | 0.00262 (11) | 0.00117 (10) |
C(10A) | 0.01157 (16) | 0.01258 (14) | 0.00885 (13) | 0.00132 (11) | 0.00339 (11) | 0.00189 (10) |
C(11A) | 0.01010 (15) | 0.01213 (13) | 0.00852 (12) | 0.00074 (11) | 0.00408 (11) | 0.00111 (10) |
N(1B) | 0.01233 (16) | 0.01339 (14) | 0.01217 (14) | 0.00169 (11) | 0.00374 (12) | 0.00190 (11) |
N(3B) | 0.0194 (2) | 0.01504 (15) | 0.01169 (14) | 0.00308 (13) | 0.00562 (14) | 0.00313 (11) |
C(2B) | 0.01486 (19) | 0.01313 (15) | 0.01525 (16) | −0.00039 (12) | 0.00782 (14) | 0.00051 (12) |
C(4B) | 0.0156 (2) | 0.01795 (17) | 0.01553 (16) | 0.00161 (14) | 0.00890 (15) | 0.00302 (13) |
C(5B) | 0.01308 (19) | 0.02019 (19) | 0.01721 (18) | 0.00434 (14) | 0.00494 (15) | 0.00217 (14) |
O(1B) | 0.0111 (2) | 0.0218 (2) | 0.0159 (2) | 0.00558 (18) | 0.00607 (18) | 0.00685 (18) |
O(2B) | 0.0144 (3) | 0.0346 (4) | 0.0125 (2) | 0.0019 (2) | 0.0038 (2) | 0.0073 (2) |
O(3B) | 0.0174 (3) | 0.0257 (3) | 0.0234 (3) | 0.0024 (2) | 0.0114 (3) | 0.0104 (2) |
O(4B) | 0.0146 (3) | 0.0262 (3) | 0.0286 (3) | 0.0080 (2) | 0.0097 (3) | 0.0085 (3) |
O(5B) | 0.0198 (3) | 0.0249 (3) | 0.0199 (3) | 0.0091 (2) | 0.0059 (2) | 0.0092 (2) |
O(6B) | 0.0238 (3) | 0.0178 (2) | 0.0191 (2) | −0.0000 (2) | 0.0144 (2) | 0.00288 (19) |
O(7B) | 0.0224 (4) | 0.0316 (4) | 0.0263 (3) | 0.0116 (3) | 0.0171 (3) | 0.0098 (3) |
N(4B) | 0.01269 (17) | 0.01383 (14) | 0.01187 (13) | 0.00148 (11) | 0.00625 (12) | 0.00192 (10) |
N(5B) | 0.01153 (17) | 0.01396 (15) | 0.01677 (16) | 0.00298 (11) | 0.00338 (13) | 0.00240 (12) |
N(6B) | 0.01318 (17) | 0.01533 (15) | 0.01292 (14) | −0.00025 (12) | 0.00726 (12) | 0.00002 (11) |
C(6B) | 0.00938 (15) | 0.01144 (13) | 0.01101 (13) | 0.00084 (10) | 0.00424 (11) | 0.00112 (10) |
C(7B) | 0.01005 (16) | 0.01094 (13) | 0.01138 (13) | 0.00071 (10) | 0.00487 (11) | 0.00113 (10) |
C(8B) | 0.01029 (16) | 0.01150 (14) | 0.01373 (15) | 0.00093 (11) | 0.00534 (12) | 0.00102 (11) |
C(9B) | 0.01033 (16) | 0.01134 (13) | 0.01315 (14) | 0.00152 (11) | 0.00401 (12) | 0.00187 (11) |
C(10B) | 0.01154 (17) | 0.01195 (14) | 0.01185 (14) | 0.00091 (11) | 0.00429 (12) | 0.00167 (10) |
C(11B) | 0.01061 (16) | 0.01130 (13) | 0.01089 (13) | 0.00017 (10) | 0.00462 (12) | 0.00057 (10) |
O(8)—C(12) | 1.2582 (7) | C(13)—H(131) | 1.0830 (4) |
O(9)—C(12) | 1.2461 (8) | C(13)—H(132) | 1.0830 (4) |
O(1A)—C(6A) | 1.2455 (7) | C(14)—H(141) | 1.0830 (5) |
O(2A)—N(4A) | 1.2329 (9) | C(14)—H(142) | 1.0830 (5) |
O(3A)—N(4A) | 1.2265 (9) | C(14)—H(143) | 1.0830 (5) |
O(4A)—N(5A) | 1.2283 (11) | C(15)—H(151) | 1.0830 (6) |
O(5A)—N(5A) | 1.2354 (9) | C(15)—H(152) | 1.0830 (7) |
O(6A)—N(6A) | 1.2353 (8) | C(15)—H(153) | 1.0830 (6) |
O(7A)—N(6A) | 1.2212 (9) | C(16)—H(161) | 1.0830 (8) |
O(1B)—C(6B) | 1.2429 (7) | C(16)—H(162) | 1.0830 (7) |
O(2B)—N(4B) | 1.2318 (8) | C(16)—H(163) | 1.0830 (6) |
O(3B)—N(4B) | 1.2251 (9) | C(2A)—H(2A) | 1.0830 (5) |
O(4B)—N(5B) | 1.2318 (11) | C(4A)—C(5A) | 1.3631 (7) |
O(5B)—N(5B) | 1.2392 (9) | C(4A)—H(4A) | 1.0830 (5) |
O(6B)—N(6B) | 1.2409 (8) | C(5A)—H(5A) | 1.0830 (6) |
O(7B)—N(6B) | 1.2246 (9) | C(6A)—C(7A) | 1.4529 (6) |
N(1A)—C(2A) | 1.3290 (7) | C(6A)—C(11A) | 1.4544 (5) |
N(1A)—C(5A) | 1.3743 (6) | C(7A)—C(8A) | 1.3864 (5) |
N(1A)—H(1A) | 1.0830 (4) | C(8A)—C(9A) | 1.3861 (5) |
N(3A)—C(2A) | 1.3330 (6) | C(8A)—H(8A) | 1.0830 (4) |
N(3A)—C(4A) | 1.3808 (7) | C(9A)—C(10A) | 1.3933 (6) |
N(3A)—H(3A) | 1.0830 (5) | C(10A)—C(11A) | 1.3706 (5) |
N(4A)—C(7A) | 1.4490 (5) | C(10A)—H(10A) | 1.0830 (4) |
N(5A)—C(9A) | 1.4460 (6) | C(2B)—H(2B) | 1.0830 (5) |
N(6A)—C(11A) | 1.4549 (6) | C(4B)—C(5B) | 1.3613 (6) |
N(1B)—C(2B) | 1.3293 (6) | C(4B)—H(4B) | 1.0830 (5) |
N(1B)—C(4B) | 1.3767 (7) | C(5B)—H(5B) | 1.0830 (5) |
N(1B)—H(1B) | 1.0830 (4) | C(6B)—C(7B) | 1.4601 (6) |
N(3B)—C(2B) | 1.3349 (6) | C(6B)—C(11B) | 1.4598 (5) |
N(3B)—C(5B) | 1.3784 (7) | C(7B)—C(8B) | 1.3785 (5) |
N(3B)—H(3B) | 1.0830 (4) | C(8B)—C(9B) | 1.3940 (6) |
N(4B)—C(7B) | 1.4553 (5) | C(8B)—H(8B) | 1.0830 (5) |
N(5B)—C(9B) | 1.4408 (6) | C(9B)—C(10B) | 1.3883 (6) |
N(6B)—C(11B) | 1.4537 (6) | C(10B)—C(11B) | 1.3796 (6) |
C(12)—C(13) | 1.5322 (5) | C(10B)—H(10B) | 1.0830 (4) |
C(2A)—N(1A)—C(5A) | 108.97 (4) | C(5A)—C(4A)—H(4A) | 131.15 (5) |
C(2A)—N(1A)—H(1A) | 122.03 (4) | N(1A)—C(5A)—C(4A) | 106.88 (5) |
C(5A)—N(1A)—H(1A) | 129.00 (5) | N(1A)—C(5A)—H(5A) | 122.06 (5) |
C(2A)—N(3A)—C(4A) | 108.50 (5) | C(4A)—C(5A)—H(5A) | 131.03 (5) |
C(2A)—N(3A)—H(3A) | 124.41 (5) | O(1A)—C(6A)—C(7A) | 126.20 (4) |
C(4A)—N(3A)—H(3A) | 126.86 (4) | O(1A)—C(6A)—C(11A) | 121.61 (5) |
O(2A)—N(4A)—O(3A) | 122.13 (6) | C(7A)—C(6A)—C(11A) | 112.14 (3) |
O(2A)—N(4A)—C(7A) | 119.52 (5) | N(4A)—C(7A)—C(6A) | 120.43 (4) |
O(3A)—N(4A)—C(7A) | 118.28 (5) | N(4A)—C(7A)—C(8A) | 116.00 (4) |
O(4A)—N(5A)—O(5A) | 123.94 (7) | C(6A)—C(7A)—C(8A) | 123.52 (3) |
O(4A)—N(5A)—C(9A) | 118.70 (6) | C(7A)—C(8A)—C(9A) | 119.52 (4) |
O(5A)—N(5A)—C(9A) | 117.36 (6) | C(7A)—C(8A)—H(8A) | 120.09 (4) |
O(6A)—N(6A)—O(7A) | 124.13 (7) | C(9A)—C(8A)—H(8A) | 120.37 (4) |
O(6A)—N(6A)—C(11A) | 117.38 (6) | N(5A)—C(9A)—C(8A) | 120.17 (4) |
O(7A)—N(6A)—C(11A) | 118.47 (5) | N(5A)—C(9A)—C(10A) | 118.56 (4) |
C(2B)—N(1B)—C(4B) | 108.99 (4) | C(8A)—C(9A)—C(10A) | 121.23 (4) |
C(2B)—N(1B)—H(1B) | 126.29 (5) | C(9A)—C(10A)—C(11A) | 118.84 (4) |
C(4B)—N(1B)—H(1B) | 124.64 (4) | C(9A)—C(10A)—H(10A) | 120.40 (4) |
C(2B)—N(3B)—C(5B) | 109.11 (4) | C(11A)—C(10A)—H(10A) | 120.71 (4) |
C(2B)—N(3B)—H(3B) | 125.20 (5) | N(6A)—C(11A)—C(6A) | 119.06 (4) |
C(5B)—N(3B)—H(3B) | 125.68 (5) | N(6A)—C(11A)—C(10A) | 116.19 (3) |
O(2B)—N(4B)—O(3B) | 122.87 (6) | C(6A)—C(11A)—C(10A) | 124.74 (4) |
O(2B)—N(4B)—C(7B) | 119.20 (6) | N(1B)—C(2B)—N(3B) | 108.24 (5) |
O(3B)—N(4B)—C(7B) | 117.92 (5) | N(1B)—C(2B)—H(2B) | 124.81 (5) |
O(4B)—N(5B)—O(5B) | 122.93 (7) | N(3B)—C(2B)—H(2B) | 126.93 (4) |
O(4B)—N(5B)—C(9B) | 118.87 (5) | N(1B)—C(4B)—C(5B) | 107.13 (4) |
O(5B)—N(5B)—C(9B) | 118.19 (6) | N(1B)—C(4B)—H(4B) | 120.91 (4) |
O(6B)—N(6B)—O(7B) | 122.79 (7) | C(5B)—C(4B)—H(4B) | 131.91 (5) |
O(6B)—N(6B)—C(11B) | 117.82 (5) | N(3B)—C(5B)—C(4B) | 106.52 (4) |
O(7B)—N(6B)—C(11B) | 119.39 (6) | N(3B)—C(5B)—H(5B) | 121.79 (5) |
O(8)—C(12)—O(9) | 126.20 (6) | C(4B)—C(5B)—H(5B) | 131.69 (5) |
O(8)—C(12)—C(13) | 113.41 (5) | O(1B)—C(6B)—C(7B) | 125.16 (5) |
O(9)—C(12)—C(13) | 120.38 (5) | O(1B)—C(6B)—C(11B) | 123.17 (5) |
C(12)—C(13)—H(131) | 106.65 (3) | C(7B)—C(6B)—C(11B) | 111.66 (3) |
C(12)—C(13)—H(132) | 107.77 (3) | N(4B)—C(7B)—C(6B) | 119.74 (4) |
H(131)—C(13)—H(132) | 111.48 (4) | N(4B)—C(7B)—C(8B) | 115.62 (4) |
H(141)—C(14)—H(142) | 112.35 (4) | C(6B)—C(7B)—C(8B) | 124.59 (4) |
H(141)—C(14)—H(143) | 110.28 (5) | C(7B)—C(8B)—C(9B) | 118.91 (4) |
H(142)—C(14)—H(143) | 111.57 (4) | C(7B)—C(8B)—H(8B) | 120.06 (4) |
H(151)—C(15)—H(152) | 114.36 (6) | C(9B)—C(8B)—H(8B) | 121.03 (4) |
H(151)—C(15)—H(153) | 108.84 (5) | N(5B)—C(9B)—C(8B) | 119.94 (4) |
H(152)—C(15)—H(153) | 111.77 (5) | N(5B)—C(9B)—C(10B) | 118.95 (4) |
H(161)—C(16)—H(162) | 111.22 (6) | C(8B)—C(9B)—C(10B) | 121.11 (4) |
H(161)—C(16)—H(163) | 113.71 (7) | C(9B)—C(10B)—C(11B) | 119.66 (4) |
H(162)—C(16)—H(163) | 111.10 (6) | C(9B)—C(10B)—H(10B) | 119.79 (4) |
N(1A)—C(2A)—N(3A) | 108.74 (4) | C(11B)—C(10B)—H(10B) | 120.55 (4) |
N(1A)—C(2A)—H(2A) | 127.08 (5) | N(6B)—C(11B)—C(6B) | 120.19 (4) |
N(3A)—C(2A)—H(2A) | 124.14 (5) | N(6B)—C(11B)—C(10B) | 115.86 (4) |
N(3A)—C(4A)—C(5A) | 106.91 (4) | C(6B)—C(11B)—C(10B) | 123.90 (4) |
N(3A)—C(4A)—H(4A) | 121.92 (5) |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | F(000) = 2944 |
Mr = 711.51 | Dx = 1.62 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -C 2yc | Cell parameters from 37970 reflections |
a = 33.5939 (5) Å | θ = 2.8–57.9° |
b = 7.66580 (8) Å | µ = 0.14 mm−1 |
c = 25.1324 (3) Å | T = 100 K |
β = 114.7162 (17)° | Block, yellow |
V = 5879.29 (13) Å3 | 0.29 × 0.21 × 0.16 mm |
Z = 8 |
SuperNova, Single source at offset, Atlas diffractometer | 27262 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 21277 reflections with > 3σ(I) |
Mirror monochromator | Rint = 0.035 |
Detector resolution: 10.3590 pixels mm-1 | θmax = 58.6°, θmin = 2.4° |
ω scans | h = −73→79 |
Absorption correction: gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | k = −17→18 |
Tmin = 0.974, Tmax = 0.982 | l = −60→60 |
165808 measured reflections |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.03 | w2 = 1/[s2(Fo2)] |
wR(F2) = 0.072 | (Δ/σ)max = 0.009 |
S = 0.87 | Δρmax = 0.31 e Å−3 |
21277 reflections | Δρmin = −0.26 e Å−3 |
1306 parameters |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | V = 5879.29 (13) Å3 |
Mr = 711.51 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 33.5939 (5) Å | µ = 0.14 mm−1 |
b = 7.66580 (8) Å | T = 100 K |
c = 25.1324 (3) Å | 0.29 × 0.21 × 0.16 mm |
β = 114.7162 (17)° |
SuperNova, Single source at offset, Atlas diffractometer | 27262 independent reflections |
Absorption correction: gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | 21277 reflections with > 3σ(I) |
Tmin = 0.974, Tmax = 0.982 | Rint = 0.035 |
165808 measured reflections |
R[F2 > 2σ(F2)] = 0.03 | 1 restraint |
wR(F2) = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.87 | Δρmax = 0.31 e Å−3 |
21277 reflections | Δρmin = −0.26 e Å−3 |
1306 parameters |
Refinement. Charge density modeled in XD2006 using the Hansen-Coppens multipole model. The heavy atoms from the multipole refinement was used to calculate anisotropic hydrogen thermal parameters using the SHADE2.1 server SHADE web server for estimation of hydrogen anisotropic displacement parameters. Anders Østergaard Madsen. J. Appl. Cryst. 39, 757–758 www.shade.ki.ku.dk |
x | y | z | Uiso*/Ueq | ||
O(8) | 0.39666 (2) | 0.11489 (8) | 0.21921 (3) | 0.015 | |
O(9) | 0.45299 (2) | −0.06032 (9) | 0.23164 (3) | 0.016 | |
N(7) | 0.405081 (15) | −0.36330 (5) | 0.239618 (17) | 0.013 | |
C(12) | 0.415166 (14) | −0.03155 (5) | 0.226991 (16) | 0.011 | |
C(13) | 0.386792 (14) | −0.18131 (5) | 0.232177 (18) | 0.011 | |
C(14) | 0.447127 (16) | −0.38055 (6) | 0.29350 (2) | 0.017 | |
C(15) | 0.371814 (19) | −0.48157 (7) | 0.24655 (3) | 0.022 | |
C(16) | 0.41140 (3) | −0.41827 (8) | 0.18684 (3) | 0.027 | |
N(1A) | 0.241477 (15) | 0.20841 (5) | 0.151236 (18) | 0.014 | |
N(3A) | 0.310061 (16) | 0.13679 (6) | 0.18950 (2) | 0.015 | |
C(2A) | 0.277876 (17) | 0.20612 (6) | 0.14255 (2) | 0.015 | |
C(4A) | 0.293445 (18) | 0.09250 (7) | 0.22950 (2) | 0.018 | |
C(5A) | 0.250264 (18) | 0.13797 (7) | 0.20529 (2) | 0.017 | |
O(1A) | 0.17910 (2) | 0.34337 (8) | 0.05774 (3) | 0.014 | |
O(2A) | 0.15299 (3) | 0.31133 (13) | 0.14452 (3) | 0.022 | |
O(3A) | 0.08584 (3) | 0.37305 (11) | 0.12522 (3) | 0.019 | |
O(4A) | 0.00250 (3) | 0.75749 (16) | −0.02871 (4) | 0.026 | |
O(5A) | 0.02422 (3) | 0.81835 (11) | −0.09687 (3) | 0.021 | |
O(6A) | 0.15056 (3) | 0.53195 (14) | −0.09916 (3) | 0.023 | |
O(7A) | 0.20503 (3) | 0.52988 (12) | −0.01320 (4) | 0.020 | |
N(4A) | 0.116993 (15) | 0.37150 (5) | 0.111794 (17) | 0.013 | |
N(5A) | 0.028543 (15) | 0.74380 (6) | −0.051189 (18) | 0.015 | |
N(6A) | 0.165869 (15) | 0.53005 (5) | −0.045110 (17) | 0.013 | |
C(6A) | 0.145345 (13) | 0.43401 (5) | 0.035482 (15) | 0.010 | |
C(7A) | 0.111414 (14) | 0.45061 (5) | 0.056754 (16) | 0.010 | |
C(8A) | 0.073337 (14) | 0.54634 (5) | 0.028220 (17) | 0.011 | |
C(9A) | 0.066836 (14) | 0.63507 (5) | −0.022817 (17) | 0.011 | |
C(10A) | 0.097484 (15) | 0.62712 (5) | −0.046708 (17) | 0.011 | |
C(11A) | 0.134983 (14) | 0.53181 (5) | −0.018275 (16) | 0.010 | |
N(1B) | 0.450749 (15) | 0.28495 (5) | 0.088229 (17) | 0.013 | |
N(3B) | 0.487950 (18) | 0.12452 (6) | 0.163266 (18) | 0.016 | |
C(2B) | 0.448402 (17) | 0.19174 (5) | 0.131425 (19) | 0.014 | |
C(4B) | 0.492900 (17) | 0.27737 (6) | 0.09240 (2) | 0.016 | |
C(5B) | 0.516455 (17) | 0.17623 (6) | 0.13969 (2) | 0.017 | |
O(1B) | 0.39645 (2) | 0.44992 (9) | −0.00919 (3) | 0.016 | |
O(2B) | 0.36247 (3) | 0.38075 (13) | 0.06819 (3) | 0.021 | |
O(3B) | 0.29181 (3) | 0.37158 (13) | 0.03035 (4) | 0.021 | |
O(4B) | 0.21289 (3) | 0.81473 (12) | −0.10836 (5) | 0.023 | |
O(5B) | 0.23659 (3) | 0.89367 (12) | −0.17292 (4) | 0.022 | |
O(6B) | 0.37848 (3) | 0.75426 (10) | −0.15044 (3) | 0.018 | |
O(7B) | 0.41174 (4) | 0.52501 (14) | −0.10190 (4) | 0.024 | |
N(4B) | 0.326352 (15) | 0.41972 (5) | 0.029624 (17) | 0.012 | |
N(5B) | 0.240827 (15) | 0.81309 (5) | −0.12811 (2) | 0.015 | |
N(6B) | 0.382634 (15) | 0.63458 (5) | −0.115264 (17) | 0.013 | |
C(6B) | 0.360806 (14) | 0.52450 (5) | −0.036526 (16) | 0.011 | |
C(7B) | 0.324122 (14) | 0.52499 (5) | −0.019731 (17) | 0.011 | |
C(8B) | 0.285522 (14) | 0.61505 (5) | −0.048880 (18) | 0.012 | |
C(9B) | 0.280376 (14) | 0.71395 (5) | −0.097881 (18) | 0.012 | |
C(10B) | 0.312667 (15) | 0.71763 (5) | −0.118729 (17) | 0.012 | |
C(11B) | 0.350824 (14) | 0.62412 (5) | −0.090103 (17) | 0.011 | |
H(131) | 0.380636 | −0.153995 | 0.270348 | 0.015 | |
H(132) | 0.356684 | −0.182908 | 0.192543 | 0.015 | |
H(141) | 0.456538 | −0.516479 | 0.29604 | 0.026 | |
H(142) | 0.440517 | −0.340699 | 0.330363 | 0.026 | |
H(143) | 0.471759 | −0.298672 | 0.288867 | 0.026 | |
H(151) | 0.342291 | −0.477075 | 0.206174 | 0.034 | |
H(152) | 0.367604 | −0.436667 | 0.284732 | 0.034 | |
H(153) | 0.38514 | −0.612419 | 0.25253 | 0.034 | |
H(161) | 0.436461 | −0.33285 | 0.184978 | 0.041 | |
H(162) | 0.380475 | −0.399768 | 0.149176 | 0.041 | |
H(163) | 0.420708 | −0.554594 | 0.192499 | 0.041 | |
H(3A) | 0.343945 | 0.129243 | 0.19583 | 0.019 | |
H(2A) | 0.281517 | 0.24812 | 0.103681 | 0.019 | |
H(4A) | 0.313499 | 0.031255 | 0.270954 | 0.022 | |
H(5A) | 0.225583 | 0.129729 | 0.222357 | 0.021 | |
H(8A) | 0.049251 | 0.554026 | 0.046318 | 0.015 | |
H(10A) | 0.092339 | 0.699669 | −0.086027 | 0.014 | |
H(1A) | 0.210977 | 0.260899 | 0.119056 | 0.017 | |
H(1B) | 0.423828 | 0.351201 | 0.053689 | 0.016 | |
H(3B) | 0.496265 | 0.043896 | 0.201829 | 0.019 | |
H(2B) | 0.418914 | 0.173 | 0.138232 | 0.018 | |
H(4B) | 0.502179 | 0.34894 | 0.062185 | 0.019 | |
H(5B) | 0.550597 | 0.137684 | 0.158882 | 0.022 | |
H(8B) | 0.259778 | 0.60826 | −0.033679 | 0.015 | |
H(10B) | 0.307506 | 0.792185 | −0.157677 | 0.015 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(8) | 0.0129 (2) | 0.01169 (19) | 0.0195 (2) | −0.00025 (15) | 0.00521 (19) | 0.00035 (16) |
O(9) | 0.0104 (2) | 0.0190 (2) | 0.0199 (2) | −0.00040 (17) | 0.00699 (19) | 0.00325 (18) |
N(7) | 0.01440 (17) | 0.01112 (13) | 0.01074 (13) | 0.00089 (11) | 0.00322 (12) | −0.00017 (10) |
C(12) | 0.00918 (16) | 0.01218 (14) | 0.01078 (13) | −0.00069 (11) | 0.00316 (11) | 0.00043 (10) |
C(13) | 0.00973 (15) | 0.01138 (13) | 0.01236 (14) | −0.00013 (10) | 0.00364 (12) | 0.00119 (10) |
C(14) | 0.01377 (19) | 0.01818 (18) | 0.01483 (17) | 0.00377 (13) | 0.00299 (14) | 0.00375 (13) |
C(15) | 0.0184 (2) | 0.01416 (17) | 0.0266 (2) | −0.00330 (15) | 0.00300 (19) | 0.00510 (15) |
C(16) | 0.0446 (4) | 0.0214 (2) | 0.0167 (2) | 0.0055 (2) | 0.0147 (2) | −0.00432 (16) |
N(1A) | 0.01152 (16) | 0.01511 (15) | 0.01195 (14) | 0.00231 (11) | 0.00251 (12) | 0.00125 (11) |
N(3A) | 0.01155 (17) | 0.01609 (16) | 0.01694 (16) | 0.00171 (12) | 0.00411 (14) | −0.00062 (12) |
C(2A) | 0.01499 (19) | 0.01494 (16) | 0.01550 (17) | 0.00159 (13) | 0.00672 (15) | 0.00267 (12) |
C(4A) | 0.0155 (2) | 0.0242 (2) | 0.01096 (15) | 0.00532 (15) | 0.00219 (14) | 0.00177 (13) |
C(5A) | 0.0148 (2) | 0.0246 (2) | 0.01284 (16) | 0.00391 (15) | 0.00593 (15) | 0.00238 (14) |
O(1A) | 0.0123 (2) | 0.0174 (2) | 0.01168 (18) | 0.00606 (16) | 0.00419 (16) | 0.00384 (15) |
O(2A) | 0.0167 (3) | 0.0346 (3) | 0.0137 (2) | 0.0062 (3) | 0.0062 (2) | 0.0110 (2) |
O(3A) | 0.0203 (3) | 0.0235 (3) | 0.0182 (2) | 0.0035 (2) | 0.0129 (2) | 0.0075 (2) |
O(4A) | 0.0168 (3) | 0.0373 (4) | 0.0225 (3) | 0.0135 (3) | 0.0079 (3) | 0.0042 (3) |
O(5A) | 0.0191 (3) | 0.0231 (3) | 0.0167 (2) | 0.0077 (2) | 0.0024 (2) | 0.0072 (2) |
O(6A) | 0.0222 (4) | 0.0370 (4) | 0.0123 (2) | −0.0045 (3) | 0.0104 (2) | −0.0010 (2) |
O(7A) | 0.0127 (3) | 0.0304 (3) | 0.0195 (3) | 0.0023 (2) | 0.0092 (2) | 0.0047 (2) |
N(4A) | 0.01370 (17) | 0.01516 (14) | 0.01031 (13) | 0.00107 (11) | 0.00560 (12) | 0.00327 (10) |
N(5A) | 0.01181 (17) | 0.01687 (16) | 0.01262 (14) | 0.00432 (12) | 0.00162 (12) | 0.00065 (12) |
N(6A) | 0.01352 (17) | 0.01585 (15) | 0.01157 (14) | 0.00015 (11) | 0.00725 (12) | 0.00055 (10) |
C(6A) | 0.00984 (15) | 0.01069 (13) | 0.00839 (12) | 0.00124 (10) | 0.00340 (11) | 0.00084 (9) |
C(7A) | 0.00985 (15) | 0.01173 (13) | 0.00892 (12) | 0.00074 (10) | 0.00402 (11) | 0.00141 (9) |
C(8A) | 0.00970 (16) | 0.01370 (14) | 0.01061 (13) | 0.00097 (11) | 0.00433 (12) | 0.00097 (10) |
C(9A) | 0.00996 (16) | 0.01264 (14) | 0.00973 (13) | 0.00178 (11) | 0.00262 (11) | 0.00117 (10) |
C(10A) | 0.01157 (16) | 0.01258 (14) | 0.00885 (13) | 0.00132 (11) | 0.00339 (11) | 0.00189 (10) |
C(11A) | 0.01010 (15) | 0.01213 (13) | 0.00852 (12) | 0.00074 (11) | 0.00408 (11) | 0.00111 (10) |
N(1B) | 0.01233 (16) | 0.01339 (14) | 0.01217 (14) | 0.00169 (11) | 0.00374 (12) | 0.00190 (11) |
N(3B) | 0.0194 (2) | 0.01504 (15) | 0.01169 (14) | 0.00308 (13) | 0.00562 (14) | 0.00313 (11) |
C(2B) | 0.01486 (19) | 0.01313 (15) | 0.01525 (16) | −0.00039 (12) | 0.00782 (14) | 0.00051 (12) |
C(4B) | 0.0156 (2) | 0.01795 (17) | 0.01553 (16) | 0.00161 (14) | 0.00890 (15) | 0.00302 (13) |
C(5B) | 0.01308 (19) | 0.02019 (19) | 0.01721 (18) | 0.00434 (14) | 0.00494 (15) | 0.00217 (14) |
O(1B) | 0.0111 (2) | 0.0218 (2) | 0.0159 (2) | 0.00558 (18) | 0.00607 (18) | 0.00685 (18) |
O(2B) | 0.0144 (3) | 0.0346 (4) | 0.0125 (2) | 0.0019 (2) | 0.0038 (2) | 0.0073 (2) |
O(3B) | 0.0174 (3) | 0.0257 (3) | 0.0234 (3) | 0.0024 (2) | 0.0114 (3) | 0.0104 (2) |
O(4B) | 0.0146 (3) | 0.0262 (3) | 0.0286 (3) | 0.0080 (2) | 0.0097 (3) | 0.0085 (3) |
O(5B) | 0.0198 (3) | 0.0249 (3) | 0.0199 (3) | 0.0091 (2) | 0.0059 (2) | 0.0092 (2) |
O(6B) | 0.0238 (3) | 0.0178 (2) | 0.0191 (2) | −0.0000 (2) | 0.0144 (2) | 0.00288 (19) |
O(7B) | 0.0224 (4) | 0.0316 (4) | 0.0263 (3) | 0.0116 (3) | 0.0171 (3) | 0.0098 (3) |
N(4B) | 0.01269 (17) | 0.01383 (14) | 0.01187 (13) | 0.00148 (11) | 0.00625 (12) | 0.00192 (10) |
N(5B) | 0.01153 (17) | 0.01396 (15) | 0.01677 (16) | 0.00298 (11) | 0.00338 (13) | 0.00240 (12) |
N(6B) | 0.01318 (17) | 0.01533 (15) | 0.01292 (14) | −0.00025 (12) | 0.00726 (12) | 0.00002 (11) |
C(6B) | 0.00938 (15) | 0.01144 (13) | 0.01101 (13) | 0.00084 (10) | 0.00424 (11) | 0.00112 (10) |
C(7B) | 0.01005 (16) | 0.01094 (13) | 0.01138 (13) | 0.00071 (10) | 0.00487 (11) | 0.00113 (10) |
C(8B) | 0.01029 (16) | 0.01150 (14) | 0.01373 (15) | 0.00093 (11) | 0.00534 (12) | 0.00102 (11) |
C(9B) | 0.01033 (16) | 0.01134 (13) | 0.01315 (14) | 0.00152 (11) | 0.00401 (12) | 0.00187 (11) |
C(10B) | 0.01154 (17) | 0.01195 (14) | 0.01185 (14) | 0.00091 (11) | 0.00429 (12) | 0.00167 (10) |
C(11B) | 0.01061 (16) | 0.01130 (13) | 0.01089 (13) | 0.00017 (10) | 0.00462 (12) | 0.00057 (10) |
H(131) | 0.040787 | 0.030270 | 0.033358 | 0.002626 | 0.026543 | 0.000576 |
H(132) | 0.021534 | 0.030480 | 0.031609 | −0.003670 | −0.004487 | 0.005556 |
H(141) | 0.043051 | 0.026026 | 0.051305 | 0.013399 | 0.009673 | 0.006372 |
H(142) | 0.042228 | 0.054338 | 0.021036 | 0.005453 | 0.011875 | −0.000770 |
H(143) | 0.024681 | 0.046948 | 0.045500 | −0.004271 | 0.010312 | 0.013709 |
H(151) | 0.034106 | 0.046419 | 0.048803 | −0.013213 | −0.007998 | 0.013075 |
H(152) | 0.049523 | 0.044397 | 0.051425 | −0.007212 | 0.031751 | 0.001975 |
H(153) | 0.049052 | 0.020668 | 0.066732 | 0.003369 | 0.018673 | 0.008672 |
H(161) | 0.066334 | 0.045327 | 0.047756 | −0.004635 | 0.040395 | −0.006920 |
H(162) | 0.067116 | 0.053989 | 0.022966 | 0.002254 | 0.003045 | −0.007358 |
H(163) | 0.096903 | 0.025887 | 0.051247 | 0.016033 | 0.038039 | −0.002700 |
H(3A) | 0.018162 | 0.038154 | 0.044230 | 0.002831 | 0.012137 | 0.000268 |
H(2A) | 0.041833 | 0.041304 | 0.031752 | 0.004268 | 0.022520 | 0.012703 |
H(4A) | 0.036805 | 0.053809 | 0.019979 | 0.014531 | 0.003088 | 0.010759 |
H(5A) | 0.032570 | 0.057958 | 0.036011 | 0.007125 | 0.023474 | 0.007602 |
H(1A) | 0.021344 | 0.034622 | 0.026395 | 0.007845 | 0.002617 | 0.005924 |
H(8A) | 0.022781 | 0.039449 | 0.029346 | 0.005375 | 0.017160 | 0.004159 |
H(10A) | 0.032016 | 0.033248 | 0.019641 | 0.004824 | 0.010754 | 0.011393 |
H(1B) | 0.020901 | 0.031690 | 0.024287 | 0.005926 | 0.006178 | 0.009555 |
H(3B) | 0.031887 | 0.032525 | 0.022999 | 0.006270 | 0.010972 | 0.011693 |
H(2B) | 0.023034 | 0.033284 | 0.032512 | 0.000048 | 0.016187 | 0.004750 |
H(4B) | 0.030058 | 0.035333 | 0.029388 | 0.001986 | 0.017977 | 0.010391 |
H(5B) | 0.018974 | 0.039798 | 0.033044 | 0.008558 | 0.008333 | 0.007312 |
H(8B) | 0.021487 | 0.035974 | 0.034230 | 0.003714 | 0.017734 | 0.006451 |
H(10B) | 0.032373 | 0.029315 | 0.022673 | 0.004664 | 0.012428 | 0.010350 |
O(8)—C(12) | 1.2582 (7) | C(13)—H(131) | 1.0830 (4) |
O(9)—C(12) | 1.2461 (8) | C(13)—H(132) | 1.0830 (4) |
O(1A)—C(6A) | 1.2455 (7) | C(14)—H(141) | 1.0830 (5) |
O(2A)—N(4A) | 1.2329 (9) | C(14)—H(142) | 1.0830 (5) |
O(3A)—N(4A) | 1.2265 (9) | C(14)—H(143) | 1.0830 (5) |
O(4A)—N(5A) | 1.2283 (11) | C(15)—H(151) | 1.0830 (6) |
O(5A)—N(5A) | 1.2354 (9) | C(15)—H(152) | 1.0830 (7) |
O(6A)—N(6A) | 1.2353 (8) | C(15)—H(153) | 1.0830 (6) |
O(7A)—N(6A) | 1.2212 (9) | C(16)—H(161) | 1.0830 (8) |
O(1B)—C(6B) | 1.2429 (7) | C(16)—H(162) | 1.0830 (7) |
O(2B)—N(4B) | 1.2318 (8) | C(16)—H(163) | 1.0830 (6) |
O(3B)—N(4B) | 1.2251 (9) | C(2A)—H(2A) | 1.0830 (5) |
O(4B)—N(5B) | 1.2318 (11) | C(4A)—C(5A) | 1.3631 (7) |
O(5B)—N(5B) | 1.2392 (9) | C(4A)—H(4A) | 1.0830 (5) |
O(6B)—N(6B) | 1.2409 (8) | C(5A)—H(5A) | 1.0830 (6) |
O(7B)—N(6B) | 1.2246 (9) | C(6A)—C(7A) | 1.4529 (6) |
N(1A)—C(2A) | 1.3290 (7) | C(6A)—C(11A) | 1.4544 (5) |
N(1A)—C(5A) | 1.3743 (6) | C(7A)—C(8A) | 1.3864 (5) |
N(1A)—H(1A) | 1.0830 (4) | C(8A)—C(9A) | 1.3861 (5) |
N(3A)—C(2A) | 1.3330 (6) | C(8A)—H(8A) | 1.0830 (4) |
N(3A)—C(4A) | 1.3808 (7) | C(9A)—C(10A) | 1.3933 (6) |
N(3A)—H(3A) | 1.0830 (5) | C(10A)—C(11A) | 1.3706 (5) |
N(4A)—C(7A) | 1.4490 (5) | C(10A)—H(10A) | 1.0830 (4) |
N(5A)—C(9A) | 1.4460 (6) | C(2B)—H(2B) | 1.0830 (5) |
N(6A)—C(11A) | 1.4549 (6) | C(4B)—C(5B) | 1.3613 (6) |
N(1B)—C(2B) | 1.3293 (6) | C(4B)—H(4B) | 1.0830 (5) |
N(1B)—C(4B) | 1.3767 (7) | C(5B)—H(5B) | 1.0830 (5) |
N(1B)—H(1B) | 1.0830 (4) | C(6B)—C(7B) | 1.4601 (6) |
N(3B)—C(2B) | 1.3349 (6) | C(6B)—C(11B) | 1.4598 (5) |
N(3B)—C(5B) | 1.3784 (7) | C(7B)—C(8B) | 1.3785 (5) |
N(3B)—H(3B) | 1.0830 (4) | C(8B)—C(9B) | 1.3940 (6) |
N(4B)—C(7B) | 1.4553 (5) | C(8B)—H(8B) | 1.0830 (5) |
N(5B)—C(9B) | 1.4408 (6) | C(9B)—C(10B) | 1.3883 (6) |
N(6B)—C(11B) | 1.4537 (6) | C(10B)—C(11B) | 1.3796 (6) |
C(12)—C(13) | 1.5322 (5) | C(10B)—H(10B) | 1.0830 (4) |
C(2A)—N(1A)—C(5A) | 108.97 (4) | C(5A)—C(4A)—H(4A) | 131.15 (5) |
C(2A)—N(1A)—H(1A) | 122.03 (4) | N(1A)—C(5A)—C(4A) | 106.88 (5) |
C(5A)—N(1A)—H(1A) | 129.00 (5) | N(1A)—C(5A)—H(5A) | 122.06 (5) |
C(2A)—N(3A)—C(4A) | 108.50 (5) | C(4A)—C(5A)—H(5A) | 131.03 (5) |
C(2A)—N(3A)—H(3A) | 124.41 (5) | O(1A)—C(6A)—C(7A) | 126.20 (4) |
C(4A)—N(3A)—H(3A) | 126.86 (4) | O(1A)—C(6A)—C(11A) | 121.61 (5) |
O(2A)—N(4A)—O(3A) | 122.13 (6) | C(7A)—C(6A)—C(11A) | 112.14 (3) |
O(2A)—N(4A)—C(7A) | 119.52 (5) | N(4A)—C(7A)—C(6A) | 120.43 (4) |
O(3A)—N(4A)—C(7A) | 118.28 (5) | N(4A)—C(7A)—C(8A) | 116.00 (4) |
O(4A)—N(5A)—O(5A) | 123.94 (7) | C(6A)—C(7A)—C(8A) | 123.52 (3) |
O(4A)—N(5A)—C(9A) | 118.70 (6) | C(7A)—C(8A)—C(9A) | 119.52 (4) |
O(5A)—N(5A)—C(9A) | 117.36 (6) | C(7A)—C(8A)—H(8A) | 120.09 (4) |
O(6A)—N(6A)—O(7A) | 124.13 (7) | C(9A)—C(8A)—H(8A) | 120.37 (4) |
O(6A)—N(6A)—C(11A) | 117.38 (6) | N(5A)—C(9A)—C(8A) | 120.17 (4) |
O(7A)—N(6A)—C(11A) | 118.47 (5) | N(5A)—C(9A)—C(10A) | 118.56 (4) |
C(2B)—N(1B)—C(4B) | 108.99 (4) | C(8A)—C(9A)—C(10A) | 121.23 (4) |
C(2B)—N(1B)—H(1B) | 126.29 (5) | C(9A)—C(10A)—C(11A) | 118.84 (4) |
C(4B)—N(1B)—H(1B) | 124.64 (4) | C(9A)—C(10A)—H(10A) | 120.40 (4) |
C(2B)—N(3B)—C(5B) | 109.11 (4) | C(11A)—C(10A)—H(10A) | 120.71 (4) |
C(2B)—N(3B)—H(3B) | 125.20 (5) | N(6A)—C(11A)—C(6A) | 119.06 (4) |
C(5B)—N(3B)—H(3B) | 125.68 (5) | N(6A)—C(11A)—C(10A) | 116.19 (3) |
O(2B)—N(4B)—O(3B) | 122.87 (6) | C(6A)—C(11A)—C(10A) | 124.74 (4) |
O(2B)—N(4B)—C(7B) | 119.20 (6) | N(1B)—C(2B)—N(3B) | 108.24 (5) |
O(3B)—N(4B)—C(7B) | 117.92 (5) | N(1B)—C(2B)—H(2B) | 124.81 (5) |
O(4B)—N(5B)—O(5B) | 122.93 (7) | N(3B)—C(2B)—H(2B) | 126.93 (4) |
O(4B)—N(5B)—C(9B) | 118.87 (5) | N(1B)—C(4B)—C(5B) | 107.13 (4) |
O(5B)—N(5B)—C(9B) | 118.19 (6) | N(1B)—C(4B)—H(4B) | 120.91 (4) |
O(6B)—N(6B)—O(7B) | 122.79 (7) | C(5B)—C(4B)—H(4B) | 131.91 (5) |
O(6B)—N(6B)—C(11B) | 117.82 (5) | N(3B)—C(5B)—C(4B) | 106.52 (4) |
O(7B)—N(6B)—C(11B) | 119.39 (6) | N(3B)—C(5B)—H(5B) | 121.79 (5) |
O(8)—C(12)—O(9) | 126.20 (6) | C(4B)—C(5B)—H(5B) | 131.69 (5) |
O(8)—C(12)—C(13) | 113.41 (5) | O(1B)—C(6B)—C(7B) | 125.16 (5) |
O(9)—C(12)—C(13) | 120.38 (5) | O(1B)—C(6B)—C(11B) | 123.17 (5) |
C(12)—C(13)—H(131) | 106.65 (3) | C(7B)—C(6B)—C(11B) | 111.66 (3) |
C(12)—C(13)—H(132) | 107.77 (3) | N(4B)—C(7B)—C(6B) | 119.74 (4) |
H(131)—C(13)—H(132) | 111.48 (4) | N(4B)—C(7B)—C(8B) | 115.62 (4) |
H(141)—C(14)—H(142) | 112.35 (4) | C(6B)—C(7B)—C(8B) | 124.59 (4) |
H(141)—C(14)—H(143) | 110.28 (5) | C(7B)—C(8B)—C(9B) | 118.91 (4) |
H(142)—C(14)—H(143) | 111.57 (4) | C(7B)—C(8B)—H(8B) | 120.06 (4) |
H(151)—C(15)—H(152) | 114.36 (6) | C(9B)—C(8B)—H(8B) | 121.03 (4) |
H(151)—C(15)—H(153) | 108.84 (5) | N(5B)—C(9B)—C(8B) | 119.94 (4) |
H(152)—C(15)—H(153) | 111.77 (5) | N(5B)—C(9B)—C(10B) | 118.95 (4) |
H(161)—C(16)—H(162) | 111.22 (6) | C(8B)—C(9B)—C(10B) | 121.11 (4) |
H(161)—C(16)—H(163) | 113.71 (7) | C(9B)—C(10B)—C(11B) | 119.66 (4) |
H(162)—C(16)—H(163) | 111.10 (6) | C(9B)—C(10B)—H(10B) | 119.79 (4) |
N(1A)—C(2A)—N(3A) | 108.74 (4) | C(11B)—C(10B)—H(10B) | 120.55 (4) |
N(1A)—C(2A)—H(2A) | 127.08 (5) | N(6B)—C(11B)—C(6B) | 120.19 (4) |
N(3A)—C(2A)—H(2A) | 124.14 (5) | N(6B)—C(11B)—C(10B) | 115.86 (4) |
N(3A)—C(4A)—C(5A) | 106.91 (4) | C(6B)—C(11B)—C(10B) | 123.90 (4) |
N(3A)—C(4A)—H(4A) | 121.92 (5) |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | F(000) = 2944 |
Mr = 711.51 | Dx = 1.62 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -C 2yc | Cell parameters from 37970 reflections |
a = 33.5939 (5) Å | θ = 2.8–57.9° |
b = 7.66580 (8) Å | µ = 0.14 mm−1 |
c = 25.1324 (3) Å | T = 100 K |
β = 114.7162 (17)° | Block, yellow |
V = 5879.29 (13) Å3 | 0.29 × 0.21 × 0.16 mm |
Z = 8 |
SuperNova, Single source at offset, Atlas diffractometer | 27262 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 21277 reflections with > 3σ(I) |
Mirror monochromator | Rint = 0.035 |
Detector resolution: 10.3590 pixels mm-1 | θmax = 58.6°, θmin = 2.4° |
ω scans | h = −73→79 |
Absorption correction: gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | k = −17→18 |
Tmin = 0.974, Tmax = 0.982 | l = −60→60 |
165808 measured reflections |
Refinement on F2 | 451 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.051 | w2 = 1/[s2(Fo2)] |
wR(F2) = 0.127 | (Δ/σ)max < 0.001 |
S = 1.51 | Δρmax = 0.90 e Å−3 |
21277 reflections | Δρmin = −0.41 e Å−3 |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | V = 5879.29 (13) Å3 |
Mr = 711.51 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 33.5939 (5) Å | µ = 0.14 mm−1 |
b = 7.66580 (8) Å | T = 100 K |
c = 25.1324 (3) Å | 0.29 × 0.21 × 0.16 mm |
β = 114.7162 (17)° |
SuperNova, Single source at offset, Atlas diffractometer | 27262 independent reflections |
Absorption correction: gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | 21277 reflections with > 3σ(I) |
Tmin = 0.974, Tmax = 0.982 | Rint = 0.035 |
165808 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 451 parameters |
wR(F2) = 0.127 | 0 restraints |
S = 1.51 | Δρmax = 0.90 e Å−3 |
21277 reflections | Δρmin = −0.41 e Å−3 |
x | y | z | Uiso*/Ueq | ||
O(8) | 0.396565 (16) | 0.11502 (6) | 0.21927 (2) | 0.016 | |
O(9) | 0.453012 (16) | −0.06047 (7) | 0.23146 (2) | 0.017 | |
N(7) | 0.405116 (18) | −0.36334 (6) | 0.23960 (2) | 0.014 | |
C(12) | 0.415179 (19) | −0.03142 (7) | 0.22700 (2) | 0.012 | |
C(13) | 0.386740 (19) | −0.18116 (7) | 0.23225 (3) | 0.012 | |
C(14) | 0.44727 (2) | −0.38086 (9) | 0.29358 (3) | 0.017 | |
C(15) | 0.37186 (2) | −0.48183 (9) | 0.24658 (4) | 0.023 | |
C(16) | 0.41167 (3) | −0.41825 (11) | 0.18679 (3) | 0.027 | |
N(1A) | 0.241536 (18) | 0.20847 (7) | 0.15125 (2) | 0.014 | |
N(3A) | 0.310008 (19) | 0.13681 (7) | 0.18955 (3) | 0.016 | |
C(2A) | 0.27780 (2) | 0.20615 (8) | 0.14250 (3) | 0.016 | |
C(4A) | 0.29340 (2) | 0.09281 (10) | 0.22947 (3) | 0.019 | |
C(5A) | 0.25035 (2) | 0.13791 (9) | 0.20534 (3) | 0.018 | |
O(1A) | 0.179118 (16) | 0.34328 (6) | 0.05781 (2) | 0.015 | |
O(2A) | 0.153076 (19) | 0.31027 (8) | 0.14442 (2) | 0.023 | |
O(3A) | 0.085774 (19) | 0.37300 (7) | 0.12528 (2) | 0.02 | |
O(4A) | 0.002560 (19) | 0.75798 (9) | −0.02861 (3) | 0.026 | |
O(5A) | 0.024114 (19) | 0.81812 (7) | −0.09697 (2) | 0.022 | |
O(6A) | 0.15050 (2) | 0.53247 (8) | −0.09921 (2) | 0.024 | |
O(7A) | 0.205065 (17) | 0.52930 (8) | −0.01323 (2) | 0.021 | |
N(4A) | 0.117005 (18) | 0.37142 (7) | 0.11180 (2) | 0.013 | |
N(5A) | 0.028569 (18) | 0.74364 (7) | −0.05122 (2) | 0.016 | |
N(6A) | 0.165910 (18) | 0.52993 (7) | −0.04507 (2) | 0.014 | |
C(6A) | 0.145359 (19) | 0.43385 (7) | 0.03553 (2) | 0.011 | |
C(7A) | 0.111426 (19) | 0.45074 (7) | 0.05668 (2) | 0.011 | |
C(8A) | 0.073264 (19) | 0.54618 (7) | 0.02827 (2) | 0.012 | |
C(9A) | 0.066927 (19) | 0.63490 (7) | −0.02274 (2) | 0.012 | |
C(10A) | 0.09742 (2) | 0.62720 (7) | −0.04673 (2) | 0.012 | |
C(11A) | 0.134983 (19) | 0.53189 (7) | −0.01821 (2) | 0.011 | |
N(1B) | 0.450823 (18) | 0.28491 (7) | 0.08818 (2) | 0.014 | |
N(3B) | 0.48790 (2) | 0.12461 (7) | 0.16322 (2) | 0.016 | |
C(2B) | 0.44834 (2) | 0.19180 (8) | 0.13144 (3) | 0.015 | |
C(4B) | 0.49290 (2) | 0.27750 (8) | 0.09248 (3) | 0.016 | |
C(5B) | 0.51639 (2) | 0.17617 (9) | 0.13961 (3) | 0.018 | |
O(1B) | 0.396515 (16) | 0.45014 (7) | −0.00908 (2) | 0.017 | |
O(2B) | 0.362615 (18) | 0.38126 (8) | 0.06828 (2) | 0.022 | |
O(3B) | 0.291819 (19) | 0.37309 (8) | 0.03071 (3) | 0.022 | |
O(4B) | 0.212816 (18) | 0.81417 (8) | −0.10830 (3) | 0.024 | |
O(5B) | 0.236568 (19) | 0.89300 (8) | −0.17303 (2) | 0.023 | |
O(6B) | 0.378519 (19) | 0.75399 (7) | −0.15053 (2) | 0.019 | |
O(7B) | 0.41191 (2) | 0.52571 (9) | −0.10155 (3) | 0.025 | |
N(4B) | 0.326311 (18) | 0.41988 (7) | 0.02963 (2) | 0.013 | |
N(5B) | 0.240831 (18) | 0.81316 (7) | −0.12805 (3) | 0.016 | |
N(6B) | 0.382655 (18) | 0.63447 (7) | −0.11522 (2) | 0.014 | |
C(6B) | 0.360836 (19) | 0.52433 (7) | −0.03650 (2) | 0.011 | |
C(7B) | 0.324109 (19) | 0.52525 (7) | −0.01979 (2) | 0.011 | |
C(8B) | 0.28552 (2) | 0.61502 (7) | −0.04885 (3) | 0.012 | |
C(9B) | 0.280535 (19) | 0.71387 (7) | −0.09774 (3) | 0.013 | |
C(10B) | 0.31256 (2) | 0.71757 (7) | −0.11880 (2) | 0.013 | |
C(11B) | 0.35077 (2) | 0.62413 (7) | −0.09007 (2) | 0.012 | |
H(131) | 0.38062 | −0.153923 | 0.270451 | 0.014669 | |
H(132) | 0.356683 | −0.182908 | 0.192542 | 0.014669 | |
H(141) | 0.456567 | −0.516904 | 0.296048 | 0.025771 | |
H(142) | 0.440527 | −0.340759 | 0.330308 | 0.025771 | |
H(143) | 0.471798 | −0.298543 | 0.28886 | 0.025771 | |
H(151) | 0.342328 | −0.477081 | 0.206224 | 0.033716 | |
H(152) | 0.367607 | −0.436702 | 0.284702 | 0.033716 | |
H(153) | 0.38517 | −0.612709 | 0.252543 | 0.033716 | |
H(161) | 0.436643 | −0.332221 | 0.184965 | 0.040908 | |
H(162) | 0.380614 | −0.39985 | 0.149343 | 0.040908 | |
H(163) | 0.420724 | −0.554832 | 0.192509 | 0.040908 | |
H(3A) | 0.343876 | 0.129258 | 0.195817 | 0.019295 | |
H(2A) | 0.281517 | 0.248118 | 0.103683 | 0.01897 | |
H(4A) | 0.313465 | 0.03136 | 0.270884 | 0.022434 | |
H(5A) | 0.225622 | 0.129742 | 0.22233 | 0.021491 | |
H(8A) | 0.049183 | 0.554048 | 0.046369 | 0.014542 | |
H(10A) | 0.092337 | 0.699693 | −0.08604 | 0.01435 | |
H(1A) | 0.211011 | 0.260841 | 0.119092 | 0.017242 | |
H(1B) | 0.423849 | 0.351149 | 0.053716 | 0.016435 | |
H(3B) | 0.496255 | 0.04399 | 0.201785 | 0.019383 | |
H(2B) | 0.418857 | 0.172964 | 0.138245 | 0.017586 | |
H(4B) | 0.502169 | 0.348866 | 0.062216 | 0.019446 | |
H(5B) | 0.550537 | 0.137751 | 0.158848 | 0.021574 | |
H(8B) | 0.259764 | 0.608256 | −0.033671 | 0.014973 | |
H(10B) | 0.307504 | 0.79221 | −0.157691 | 0.015326 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(8) | 0.0145 (2) | 0.01229 (16) | 0.01919 (19) | −0.00029 (13) | 0.00504 (15) | 0.00036 (13) |
O(9) | 0.01053 (19) | 0.0206 (2) | 0.0195 (2) | 0.00020 (14) | 0.00663 (16) | 0.00336 (15) |
N(7) | 0.0153 (2) | 0.01187 (17) | 0.01139 (17) | 0.00092 (14) | 0.00354 (15) | −0.00015 (13) |
C(12) | 0.0104 (2) | 0.01341 (19) | 0.00978 (18) | −0.00141 (15) | 0.00281 (16) | 0.00018 (14) |
C(13) | 0.0110 (2) | 0.01156 (19) | 0.0134 (2) | 0.00019 (15) | 0.00389 (17) | 0.00146 (15) |
C(14) | 0.0143 (3) | 0.0190 (2) | 0.0150 (2) | 0.00412 (18) | 0.00280 (19) | 0.00393 (18) |
C(15) | 0.0188 (3) | 0.0148 (2) | 0.0276 (3) | −0.0041 (2) | 0.0034 (2) | 0.0051 (2) |
C(16) | 0.0437 (5) | 0.0222 (3) | 0.0173 (3) | 0.0057 (3) | 0.0144 (3) | −0.0045 (2) |
N(1A) | 0.0128 (2) | 0.01543 (19) | 0.01227 (18) | 0.00194 (15) | 0.00284 (15) | 0.00081 (14) |
N(3A) | 0.0133 (2) | 0.0156 (2) | 0.0179 (2) | 0.00146 (16) | 0.00456 (17) | −0.00109 (16) |
C(2A) | 0.0165 (3) | 0.0145 (2) | 0.0164 (2) | 0.00135 (18) | 0.0066 (2) | 0.00173 (17) |
C(4A) | 0.0165 (3) | 0.0246 (3) | 0.0118 (2) | 0.0048 (2) | 0.00279 (19) | 0.00121 (18) |
C(5A) | 0.0169 (3) | 0.0241 (3) | 0.0130 (2) | 0.0039 (2) | 0.0059 (2) | 0.00207 (18) |
O(1A) | 0.01297 (19) | 0.01732 (18) | 0.01267 (16) | 0.00545 (14) | 0.00429 (14) | 0.00306 (13) |
O(2A) | 0.0179 (2) | 0.0343 (3) | 0.01435 (19) | 0.00631 (19) | 0.00492 (17) | 0.01054 (17) |
O(3A) | 0.0209 (2) | 0.0243 (2) | 0.0195 (2) | 0.00232 (17) | 0.01348 (19) | 0.00649 (16) |
O(4A) | 0.0171 (2) | 0.0381 (3) | 0.0234 (2) | 0.0116 (2) | 0.0083 (2) | 0.0031 (2) |
O(5A) | 0.0216 (2) | 0.0235 (2) | 0.0163 (2) | 0.00652 (18) | 0.00237 (17) | 0.00691 (16) |
O(6A) | 0.0251 (3) | 0.0369 (3) | 0.01191 (18) | −0.0039 (2) | 0.01062 (18) | −0.00104 (17) |
O(7A) | 0.0127 (2) | 0.0298 (3) | 0.0211 (2) | 0.00211 (17) | 0.00837 (17) | 0.00488 (18) |
N(4A) | 0.0148 (2) | 0.01460 (19) | 0.01117 (17) | 0.00070 (15) | 0.00598 (16) | 0.00260 (13) |
N(5A) | 0.0128 (2) | 0.0170 (2) | 0.01329 (19) | 0.00355 (16) | 0.00132 (16) | −0.00035 (15) |
N(6A) | 0.0151 (2) | 0.01540 (19) | 0.01241 (18) | 0.00016 (15) | 0.00771 (16) | 0.00064 (14) |
C(6A) | 0.0109 (2) | 0.01110 (18) | 0.00880 (17) | 0.00030 (14) | 0.00343 (15) | 0.00008 (13) |
C(7A) | 0.0114 (2) | 0.01217 (19) | 0.00904 (17) | −0.00003 (15) | 0.00411 (15) | 0.00104 (13) |
C(8A) | 0.0109 (2) | 0.0135 (2) | 0.01104 (18) | 0.00025 (15) | 0.00405 (16) | 0.00026 (14) |
C(9A) | 0.0105 (2) | 0.01285 (19) | 0.01079 (19) | 0.00165 (15) | 0.00238 (16) | 0.00054 (14) |
C(10A) | 0.0127 (2) | 0.01243 (19) | 0.00945 (18) | 0.00041 (15) | 0.00348 (16) | 0.00092 (14) |
C(11A) | 0.0113 (2) | 0.01249 (18) | 0.00930 (17) | −0.00007 (15) | 0.00460 (15) | 0.00031 (14) |
N(1B) | 0.0135 (2) | 0.01373 (18) | 0.01296 (18) | 0.00111 (14) | 0.00441 (16) | 0.00105 (14) |
N(3B) | 0.0195 (2) | 0.0155 (2) | 0.01254 (19) | 0.00275 (17) | 0.00569 (17) | 0.00228 (15) |
C(2B) | 0.0163 (3) | 0.0132 (2) | 0.0160 (2) | −0.00041 (17) | 0.00811 (19) | −0.00018 (16) |
C(4B) | 0.0164 (3) | 0.0181 (2) | 0.0164 (2) | 0.00129 (19) | 0.0090 (2) | 0.00179 (18) |
C(5B) | 0.0153 (3) | 0.0200 (3) | 0.0180 (2) | 0.0037 (2) | 0.0059 (2) | 0.00095 (19) |
O(1B) | 0.01230 (19) | 0.0214 (2) | 0.01652 (18) | 0.00491 (15) | 0.00589 (15) | 0.00545 (14) |
O(2B) | 0.0154 (2) | 0.0346 (3) | 0.01265 (18) | 0.00237 (18) | 0.00287 (16) | 0.00637 (17) |
O(3B) | 0.0174 (2) | 0.0270 (2) | 0.0258 (2) | 0.00164 (18) | 0.01260 (19) | 0.01018 (19) |
O(4B) | 0.0147 (2) | 0.0269 (3) | 0.0304 (3) | 0.00689 (18) | 0.0102 (2) | 0.0073 (2) |
O(5B) | 0.0214 (2) | 0.0248 (2) | 0.0196 (2) | 0.00759 (18) | 0.00555 (19) | 0.00893 (17) |
O(6B) | 0.0248 (2) | 0.01807 (19) | 0.0190 (2) | −0.00078 (17) | 0.01399 (18) | 0.00296 (15) |
O(7B) | 0.0218 (3) | 0.0332 (3) | 0.0273 (3) | 0.0123 (2) | 0.0164 (2) | 0.0097 (2) |
N(4B) | 0.0143 (2) | 0.01345 (18) | 0.01229 (17) | 0.00139 (14) | 0.00648 (16) | 0.00095 (13) |
N(5B) | 0.0124 (2) | 0.01405 (19) | 0.0173 (2) | 0.00241 (15) | 0.00338 (17) | 0.00155 (15) |
N(6B) | 0.0141 (2) | 0.0159 (2) | 0.01290 (18) | −0.00119 (15) | 0.00684 (16) | −0.00097 (14) |
C(6B) | 0.0110 (2) | 0.01129 (18) | 0.01143 (18) | 0.00011 (15) | 0.00426 (16) | 0.00011 (14) |
C(7B) | 0.0117 (2) | 0.01103 (18) | 0.01174 (18) | 0.00041 (15) | 0.00525 (16) | 0.00079 (14) |
C(8B) | 0.0119 (2) | 0.01139 (19) | 0.0138 (2) | 0.00039 (15) | 0.00529 (17) | 0.00016 (15) |
C(9B) | 0.0106 (2) | 0.01160 (19) | 0.0140 (2) | 0.00133 (15) | 0.00365 (17) | 0.00139 (15) |
C(10B) | 0.0133 (2) | 0.01193 (19) | 0.01217 (19) | 0.00041 (16) | 0.00443 (17) | 0.00083 (15) |
C(11B) | 0.0118 (2) | 0.01211 (19) | 0.01168 (19) | −0.00033 (15) | 0.00551 (16) | 0.00016 (14) |
O(8)—C(12) | 1.2599 (8) | C(13)—H(131) | 1.0830 (6) |
O(9)—C(12) | 1.2484 (8) | C(13)—H(132) | 1.0830 (6) |
O(1A)—C(6A) | 1.2452 (7) | C(14)—H(141) | 1.0830 (7) |
O(2A)—N(4A) | 1.2367 (8) | C(14)—H(142) | 1.0830 (7) |
O(3A)—N(4A) | 1.2300 (8) | C(14)—H(143) | 1.0830 (7) |
O(4A)—N(5A) | 1.2302 (9) | C(15)—H(151) | 1.0830 (7) |
O(5A)—N(5A) | 1.2355 (8) | C(15)—H(152) | 1.0830 (9) |
O(6A)—N(6A) | 1.2372 (7) | C(15)—H(153) | 1.0830 (7) |
O(7A)—N(6A) | 1.2208 (8) | C(16)—H(161) | 1.0830 (10) |
O(1B)—C(6B) | 1.2427 (8) | C(16)—H(162) | 1.0830 (9) |
O(2B)—N(4B) | 1.2362 (7) | C(16)—H(163) | 1.0830 (8) |
O(3B)—N(4B) | 1.2241 (8) | C(2A)—H(2A) | 1.0830 (7) |
O(4B)—N(5B) | 1.2339 (9) | C(4A)—C(5A) | 1.3584 (10) |
O(5B)—N(5B) | 1.2402 (8) | C(4A)—H(4A) | 1.0830 (6) |
O(6B)—N(6B) | 1.2424 (7) | C(5A)—H(5A) | 1.0830 (7) |
O(7B)—N(6B) | 1.2233 (8) | C(6A)—C(7A) | 1.4510 (8) |
N(1A)—C(2A) | 1.3254 (9) | C(6A)—C(11A) | 1.4550 (7) |
N(1A)—C(5A) | 1.3755 (8) | C(7A)—C(8A) | 1.3868 (8) |
N(1A)—H(1A) | 1.0830 (5) | C(8A)—C(9A) | 1.3867 (8) |
N(3A)—C(2A) | 1.3348 (8) | C(8A)—H(8A) | 1.0830 (6) |
N(3A)—C(4A) | 1.3782 (10) | C(9A)—C(10A) | 1.3904 (9) |
N(3A)—H(3A) | 1.0830 (6) | C(10A)—C(11A) | 1.3724 (8) |
N(4A)—C(7A) | 1.4514 (7) | C(10A)—H(10A) | 1.0830 (5) |
N(5A)—C(9A) | 1.4479 (8) | C(2B)—H(2B) | 1.0830 (7) |
N(6A)—C(11A) | 1.4567 (8) | C(4B)—C(5B) | 1.3593 (9) |
N(1B)—C(2B) | 1.3320 (8) | C(4B)—H(4B) | 1.0830 (6) |
N(1B)—C(4B) | 1.3729 (9) | C(5B)—H(5B) | 1.0830 (7) |
N(1B)—H(1B) | 1.0830 (5) | C(6B)—C(7B) | 1.4601 (8) |
N(3B)—C(2B) | 1.3348 (9) | C(6B)—C(11B) | 1.4600 (8) |
N(3B)—C(5B) | 1.3777 (10) | C(7B)—C(8B) | 1.3768 (8) |
N(3B)—H(3B) | 1.0830 (5) | C(8B)—C(9B) | 1.3929 (8) |
N(4B)—C(7B) | 1.4573 (7) | C(8B)—H(8B) | 1.0830 (6) |
N(5B)—C(9B) | 1.4453 (8) | C(9B)—C(10B) | 1.3837 (9) |
N(6B)—C(11B) | 1.4557 (8) | C(10B)—C(11B) | 1.3808 (8) |
C(12)—C(13) | 1.5340 (8) | C(10B)—H(10B) | 1.0830 (6) |
C(2A)—N(1A)—C(5A) | 109.01 (5) | C(5A)—C(4A)—H(4A) | 131.17 (7) |
C(2A)—N(1A)—H(1A) | 122.03 (5) | N(1A)—C(5A)—C(4A) | 106.88 (6) |
C(5A)—N(1A)—H(1A) | 128.96 (6) | N(1A)—C(5A)—H(5A) | 121.92 (6) |
C(2A)—N(3A)—C(4A) | 108.50 (6) | C(4A)—C(5A)—H(5A) | 131.17 (6) |
C(2A)—N(3A)—H(3A) | 124.28 (6) | O(1A)—C(6A)—C(7A) | 126.32 (5) |
C(4A)—N(3A)—H(3A) | 126.98 (6) | O(1A)—C(6A)—C(11A) | 121.67 (5) |
O(2A)—N(4A)—O(3A) | 122.23 (5) | C(7A)—C(6A)—C(11A) | 111.96 (5) |
O(2A)—N(4A)—C(7A) | 119.42 (5) | N(4A)—C(7A)—C(6A) | 120.30 (5) |
O(3A)—N(4A)—C(7A) | 118.30 (5) | N(4A)—C(7A)—C(8A) | 115.80 (5) |
O(4A)—N(5A)—O(5A) | 123.74 (6) | C(6A)—C(7A)—C(8A) | 123.86 (5) |
O(4A)—N(5A)—C(9A) | 118.70 (6) | C(7A)—C(8A)—C(9A) | 119.10 (5) |
O(5A)—N(5A)—C(9A) | 117.55 (6) | C(7A)—C(8A)—H(8A) | 120.34 (5) |
O(6A)—N(6A)—O(7A) | 124.17 (6) | C(9A)—C(8A)—H(8A) | 120.54 (5) |
O(6A)—N(6A)—C(11A) | 117.26 (5) | N(5A)—C(9A)—C(8A) | 120.02 (6) |
O(7A)—N(6A)—C(11A) | 118.56 (5) | N(5A)—C(9A)—C(10A) | 118.35 (5) |
C(2B)—N(1B)—C(4B) | 109.11 (5) | C(8A)—C(9A)—C(10A) | 121.60 (5) |
C(2B)—N(1B)—H(1B) | 125.95 (6) | C(9A)—C(10A)—C(11A) | 118.65 (5) |
C(4B)—N(1B)—H(1B) | 124.88 (5) | C(9A)—C(10A)—H(10A) | 120.67 (5) |
C(2B)—N(3B)—C(5B) | 109.19 (5) | C(11A)—C(10A)—H(10A) | 120.63 (6) |
C(2B)—N(3B)—H(3B) | 125.18 (6) | N(6A)—C(11A)—C(6A) | 118.98 (5) |
C(5B)—N(3B)—H(3B) | 125.62 (6) | N(6A)—C(11A)—C(10A) | 116.21 (5) |
O(2B)—N(4B)—O(3B) | 122.98 (6) | C(6A)—C(11A)—C(10A) | 124.81 (5) |
O(2B)—N(4B)—C(7B) | 118.97 (5) | N(1B)—C(2B)—N(3B) | 107.98 (6) |
O(3B)—N(4B)—C(7B) | 118.04 (5) | N(1B)—C(2B)—H(2B) | 125.02 (6) |
O(4B)—N(5B)—O(5B) | 123.15 (6) | N(3B)—C(2B)—H(2B) | 126.99 (6) |
O(4B)—N(5B)—C(9B) | 118.84 (5) | N(1B)—C(4B)—C(5B) | 107.19 (6) |
O(5B)—N(5B)—C(9B) | 118.01 (6) | N(1B)—C(4B)—H(4B) | 120.85 (6) |
O(6B)—N(6B)—O(7B) | 122.68 (6) | C(5B)—C(4B)—H(4B) | 131.92 (7) |
O(6B)—N(6B)—C(11B) | 117.87 (5) | N(3B)—C(5B)—C(4B) | 106.53 (6) |
O(7B)—N(6B)—C(11B) | 119.44 (5) | N(3B)—C(5B)—H(5B) | 121.78 (6) |
O(8)—C(12)—O(9) | 126.43 (6) | C(4B)—C(5B)—H(5B) | 131.68 (7) |
O(8)—C(12)—C(13) | 113.15 (5) | O(1B)—C(6B)—C(7B) | 125.29 (5) |
O(9)—C(12)—C(13) | 120.41 (5) | O(1B)—C(6B)—C(11B) | 123.31 (6) |
C(12)—C(13)—H(131) | 106.73 (5) | C(7B)—C(6B)—C(11B) | 111.40 (5) |
C(12)—C(13)—H(132) | 107.72 (5) | N(4B)—C(7B)—C(6B) | 119.64 (5) |
H(131)—C(13)—H(132) | 111.70 (5) | N(4B)—C(7B)—C(8B) | 115.47 (5) |
H(141)—C(14)—H(142) | 112.49 (6) | C(6B)—C(7B)—C(8B) | 124.84 (5) |
H(141)—C(14)—H(143) | 110.67 (6) | C(7B)—C(8B)—C(9B) | 118.62 (6) |
H(142)—C(14)—H(143) | 111.58 (6) | C(7B)—C(8B)—H(8B) | 120.20 (5) |
H(151)—C(15)—H(152) | 114.18 (8) | C(9B)—C(8B)—H(8B) | 121.18 (5) |
H(151)—C(15)—H(153) | 108.92 (7) | N(5B)—C(9B)—C(8B) | 119.70 (6) |
H(152)—C(15)—H(153) | 111.89 (7) | N(5B)—C(9B)—C(10B) | 118.78 (5) |
H(161)—C(16)—H(162) | 111.46 (7) | C(8B)—C(9B)—C(10B) | 121.51 (5) |
H(161)—C(16)—H(163) | 114.51 (8) | C(9B)—C(10B)—C(11B) | 119.40 (5) |
H(162)—C(16)—H(163) | 110.87 (7) | C(9B)—C(10B)—H(10B) | 120.15 (5) |
N(1A)—C(2A)—N(3A) | 108.62 (6) | C(11B)—C(10B)—H(10B) | 120.45 (6) |
N(1A)—C(2A)—H(2A) | 127.28 (6) | N(6B)—C(11B)—C(6B) | 120.00 (5) |
N(3A)—C(2A)—H(2A) | 124.07 (6) | N(6B)—C(11B)—C(10B) | 115.89 (5) |
N(3A)—C(4A)—C(5A) | 106.99 (6) | C(6B)—C(11B)—C(10B) | 124.07 (6) |
N(3A)—C(4A)—H(4A) | 121.82 (6) |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | F(000) = 2944 |
Mr = 711.51 | Dx = 1.62 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -C 2yc | Cell parameters from 37970 reflections |
a = 33.5939 (5) Å | θ = 2.8–57.9° |
b = 7.66580 (8) Å | µ = 0.14 mm−1 |
c = 25.1324 (3) Å | T = 100 K |
β = 114.7162 (17)° | Block, yellow |
V = 5879.29 (13) Å3 | 0.29 × 0.21 × 0.16 mm |
Z = 8 |
SuperNova, Single source at offset, Atlas diffractometer | 27262 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 21277 reflections with > 3σ(I) |
Mirror monochromator | Rint = 0.035 |
Detector resolution: 10.3590 pixels mm-1 | θmax = 58.6°, θmin = 2.4° |
ω scans | h = −73→79 |
Absorption correction: gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | k = −17→18 |
Tmin = 0.974, Tmax = 0.982 | l = −60→60 |
165808 measured reflections |
Refinement on F2 | 451 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.056 | w2 = 1/[s2(Fo2)] |
wR(F2) = 0.166 | (Δ/σ)max < 0.001 |
S = 0.8 | Δρmax = 0.19 e Å−3 |
10569 reflections | Δρmin = −0.21 e Å−3 |
2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | V = 5879.29 (13) Å3 |
Mr = 711.51 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 33.5939 (5) Å | µ = 0.14 mm−1 |
b = 7.66580 (8) Å | T = 100 K |
c = 25.1324 (3) Å | 0.29 × 0.21 × 0.16 mm |
β = 114.7162 (17)° |
SuperNova, Single source at offset, Atlas diffractometer | 27262 independent reflections |
Absorption correction: gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | 21277 reflections with > 3σ(I) |
Tmin = 0.974, Tmax = 0.982 | Rint = 0.035 |
165808 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 451 parameters |
wR(F2) = 0.166 | 0 restraints |
S = 0.8 | Δρmax = 0.19 e Å−3 |
10569 reflections | Δρmin = −0.21 e Å−3 |
x | y | z | Uiso*/Ueq | ||
O(8) | 0.39663 (3) | 0.11491 (8) | 0.21924 (3) | 0.016 | |
O(9) | 0.45300 (3) | −0.06029 (10) | 0.23162 (4) | 0.017 | |
N(7) | 0.40509 (3) | −0.36340 (8) | 0.23966 (3) | 0.013 | |
C(12) | 0.41515 (2) | −0.03140 (8) | 0.22703 (3) | 0.011 | |
C(13) | 0.38676 (2) | −0.18135 (9) | 0.23223 (3) | 0.012 | |
C(14) | 0.44715 (3) | −0.38043 (12) | 0.29359 (4) | 0.017 | |
C(15) | 0.37178 (4) | −0.48155 (13) | 0.24668 (6) | 0.022 | |
C(16) | 0.41120 (7) | −0.41793 (17) | 0.18672 (5) | 0.027 | |
N(1A) | 0.24150 (3) | 0.20832 (9) | 0.15123 (3) | 0.014 | |
N(3A) | 0.31007 (3) | 0.13670 (10) | 0.18956 (4) | 0.016 | |
C(2A) | 0.27788 (3) | 0.20599 (11) | 0.14261 (4) | 0.016 | |
C(4A) | 0.29337 (4) | 0.09201 (14) | 0.22952 (3) | 0.018 | |
C(5A) | 0.25018 (4) | 0.13769 (15) | 0.20525 (4) | 0.018 | |
O(1A) | 0.17914 (2) | 0.34337 (9) | 0.05776 (3) | 0.014 | |
O(2A) | 0.15304 (3) | 0.31125 (16) | 0.14452 (4) | 0.022 | |
O(3A) | 0.08581 (4) | 0.37303 (13) | 0.12520 (4) | 0.019 | |
O(4A) | 0.00255 (4) | 0.7579 (2) | −0.02859 (5) | 0.026 | |
O(5A) | 0.02423 (4) | 0.81834 (13) | −0.09685 (4) | 0.022 | |
O(6A) | 0.15053 (4) | 0.53241 (18) | −0.09916 (3) | 0.023 | |
O(7A) | 0.20502 (3) | 0.52961 (15) | −0.01319 (4) | 0.02 | |
N(4A) | 0.11701 (3) | 0.37161 (9) | 0.11184 (3) | 0.013 | |
N(5A) | 0.02853 (3) | 0.74372 (10) | −0.05119 (3) | 0.015 | |
N(6A) | 0.16588 (3) | 0.53021 (9) | −0.04507 (3) | 0.013 | |
C(6A) | 0.14532 (2) | 0.43377 (8) | 0.03551 (2) | 0.01 | |
C(7A) | 0.11140 (2) | 0.45077 (8) | 0.05675 (3) | 0.011 | |
C(8A) | 0.07330 (3) | 0.54625 (9) | 0.02825 (3) | 0.012 | |
C(9A) | 0.06683 (3) | 0.63502 (9) | −0.02283 (3) | 0.012 | |
C(10A) | 0.09755 (3) | 0.62719 (9) | −0.04670 (3) | 0.012 | |
C(11A) | 0.13496 (2) | 0.53184 (8) | −0.01829 (3) | 0.011 | |
N(1B) | 0.45077 (3) | 0.28490 (8) | 0.08822 (3) | 0.013 | |
N(3B) | 0.48798 (3) | 0.12449 (10) | 0.16322 (3) | 0.016 | |
C(2B) | 0.44846 (3) | 0.19173 (10) | 0.13142 (3) | 0.014 | |
C(4B) | 0.49293 (4) | 0.27742 (12) | 0.09250 (4) | 0.016 | |
C(5B) | 0.51648 (3) | 0.17618 (13) | 0.13970 (4) | 0.018 | |
O(1B) | 0.39643 (3) | 0.44970 (11) | −0.00921 (3) | 0.016 | |
O(2B) | 0.36246 (3) | 0.38078 (16) | 0.06822 (3) | 0.022 | |
O(3B) | 0.29177 (4) | 0.37200 (15) | 0.03036 (5) | 0.021 | |
O(4B) | 0.21292 (4) | 0.81462 (16) | −0.10830 (6) | 0.023 | |
O(5B) | 0.23665 (4) | 0.89352 (14) | −0.17295 (4) | 0.022 | |
O(6B) | 0.37845 (4) | 0.75421 (11) | −0.15043 (4) | 0.019 | |
O(7B) | 0.41170 (5) | 0.52502 (18) | −0.10196 (5) | 0.024 | |
N(4B) | 0.32629 (3) | 0.41964 (8) | 0.02961 (3) | 0.013 | |
N(5B) | 0.24082 (3) | 0.81299 (9) | −0.12813 (3) | 0.015 | |
N(6B) | 0.38267 (3) | 0.63451 (9) | −0.11525 (3) | 0.014 | |
C(6B) | 0.36083 (2) | 0.52452 (8) | −0.03655 (3) | 0.011 | |
C(7B) | 0.32406 (3) | 0.52516 (8) | −0.01980 (3) | 0.011 | |
C(8B) | 0.28554 (3) | 0.61509 (9) | −0.04889 (3) | 0.012 | |
C(9B) | 0.28040 (3) | 0.71400 (9) | −0.09786 (3) | 0.013 | |
C(10B) | 0.31269 (3) | 0.71765 (9) | −0.11868 (3) | 0.012 | |
C(11B) | 0.35085 (3) | 0.62410 (8) | −0.09011 (3) | 0.011 | |
H(131) | 0.380625 | −0.153945 | 0.27042 | 0.014669 | |
H(132) | 0.356686 | −0.182908 | 0.192546 | 0.014669 | |
H(141) | 0.45653 | −0.516368 | 0.296038 | 0.025771 | |
H(142) | 0.440505 | −0.340626 | 0.330431 | 0.025771 | |
H(143) | 0.471762 | −0.298661 | 0.288867 | 0.025771 | |
H(151) | 0.342328 | −0.477081 | 0.206223 | 0.033716 | |
H(152) | 0.367589 | −0.436508 | 0.284866 | 0.033716 | |
H(153) | 0.385132 | −0.61234 | 0.252527 | 0.033716 | |
H(161) | 0.436396 | −0.333052 | 0.184982 | 0.040908 | |
H(162) | 0.380313 | −0.399672 | 0.148975 | 0.040908 | |
H(163) | 0.420671 | −0.554067 | 0.192477 | 0.040908 | |
H(3A) | 0.343945 | 0.129243 | 0.19583 | 0.019295 | |
H(2A) | 0.281512 | 0.248062 | 0.103735 | 0.01897 | |
H(4A) | 0.313527 | 0.031174 | 0.271011 | 0.022434 | |
H(5A) | 0.225539 | 0.129715 | 0.222388 | 0.021491 | |
H(8A) | 0.049214 | 0.554038 | 0.046346 | 0.014542 | |
H(10A) | 0.092336 | 0.699706 | −0.086047 | 0.01435 | |
H(1A) | 0.210997 | 0.260865 | 0.119077 | 0.017242 | |
H(1B) | 0.42384 | 0.351171 | 0.053705 | 0.016435 | |
H(3B) | 0.496257 | 0.043968 | 0.201796 | 0.019383 | |
H(2B) | 0.418964 | 0.173032 | 0.13822 | 0.017586 | |
H(4B) | 0.50217 | 0.34887 | 0.062214 | 0.019446 | |
H(5B) | 0.550624 | 0.137652 | 0.158897 | 0.021574 | |
H(8B) | 0.259797 | 0.608265 | −0.03369 | 0.014973 | |
H(10B) | 0.307509 | 0.792133 | −0.157651 | 0.015326 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(8) | 0.0137 (2) | 0.01197 (17) | 0.0196 (2) | −0.00017 (13) | 0.00528 (16) | 0.00037 (13) |
O(9) | 0.0105 (2) | 0.0199 (2) | 0.0199 (2) | −0.00023 (15) | 0.00698 (17) | 0.00307 (16) |
N(7) | 0.0148 (2) | 0.01144 (16) | 0.01112 (16) | 0.00076 (13) | 0.00331 (14) | −0.00022 (11) |
C(12) | 0.0098 (2) | 0.01260 (18) | 0.01089 (17) | −0.00080 (13) | 0.00339 (14) | 0.00038 (12) |
C(13) | 0.0099 (2) | 0.01181 (17) | 0.01321 (18) | 0.00010 (13) | 0.00390 (15) | 0.00145 (13) |
C(14) | 0.0141 (3) | 0.0189 (3) | 0.0155 (2) | 0.00356 (18) | 0.0032 (2) | 0.00385 (17) |
C(15) | 0.0190 (4) | 0.0147 (2) | 0.0264 (4) | −0.0034 (2) | 0.0037 (3) | 0.0047 (2) |
C(16) | 0.0429 (8) | 0.0214 (3) | 0.0172 (3) | 0.0057 (4) | 0.0142 (4) | −0.0041 (2) |
N(1A) | 0.0121 (2) | 0.01525 (19) | 0.01250 (17) | 0.00227 (13) | 0.00270 (15) | 0.00129 (13) |
N(3A) | 0.0123 (2) | 0.0161 (2) | 0.0171 (2) | 0.00161 (14) | 0.00426 (17) | −0.00074 (15) |
C(2A) | 0.0155 (3) | 0.0155 (2) | 0.0160 (2) | 0.00135 (17) | 0.00697 (19) | 0.00247 (16) |
C(4A) | 0.0164 (3) | 0.0239 (3) | 0.0117 (2) | 0.0052 (2) | 0.00271 (19) | 0.00177 (18) |
C(5A) | 0.0152 (3) | 0.0249 (3) | 0.0130 (2) | 0.0038 (2) | 0.0058 (2) | 0.00239 (18) |
O(1A) | 0.0128 (2) | 0.01745 (19) | 0.01228 (16) | 0.00598 (14) | 0.00433 (14) | 0.00339 (12) |
O(2A) | 0.0172 (3) | 0.0339 (4) | 0.0144 (2) | 0.0069 (2) | 0.00588 (19) | 0.0109 (2) |
O(3A) | 0.0202 (3) | 0.0241 (3) | 0.0194 (2) | 0.0032 (2) | 0.0136 (2) | 0.00714 (19) |
O(4A) | 0.0167 (4) | 0.0380 (5) | 0.0229 (3) | 0.0123 (3) | 0.0084 (3) | 0.0039 (3) |
O(5A) | 0.0197 (3) | 0.0231 (3) | 0.0168 (2) | 0.0073 (2) | 0.00268 (19) | 0.00719 (18) |
O(6A) | 0.0230 (4) | 0.0369 (4) | 0.0121 (2) | −0.0048 (3) | 0.0101 (2) | −0.00134 (19) |
O(7A) | 0.0127 (3) | 0.0303 (3) | 0.0199 (2) | 0.0023 (2) | 0.0085 (2) | 0.0050 (2) |
N(4A) | 0.0146 (2) | 0.01526 (19) | 0.01063 (16) | 0.00084 (14) | 0.00571 (15) | 0.00306 (12) |
N(5A) | 0.0122 (2) | 0.0173 (2) | 0.01331 (18) | 0.00445 (15) | 0.00194 (16) | 0.00054 (14) |
N(6A) | 0.0139 (2) | 0.01587 (19) | 0.01207 (17) | −0.00002 (14) | 0.00744 (15) | 0.00050 (12) |
C(6A) | 0.0102 (2) | 0.01092 (17) | 0.00901 (15) | 0.00101 (12) | 0.00345 (13) | 0.00060 (11) |
C(7A) | 0.0106 (2) | 0.01196 (17) | 0.00954 (16) | 0.00048 (13) | 0.00437 (14) | 0.00131 (11) |
C(8A) | 0.0103 (2) | 0.01394 (19) | 0.01129 (17) | 0.00076 (14) | 0.00467 (15) | 0.00084 (13) |
C(9A) | 0.0102 (2) | 0.01305 (19) | 0.01058 (17) | 0.00186 (13) | 0.00299 (14) | 0.00106 (12) |
C(10A) | 0.0122 (2) | 0.01266 (18) | 0.00945 (16) | 0.00097 (13) | 0.00345 (14) | 0.00159 (12) |
C(11A) | 0.0108 (2) | 0.01219 (18) | 0.00920 (16) | 0.00068 (13) | 0.00434 (14) | 0.00082 (12) |
N(1B) | 0.0124 (2) | 0.01375 (18) | 0.01268 (17) | 0.00163 (13) | 0.00401 (15) | 0.00153 (12) |
N(3B) | 0.0189 (3) | 0.0158 (2) | 0.01222 (18) | 0.00312 (16) | 0.00581 (17) | 0.00276 (13) |
C(2B) | 0.0151 (3) | 0.0136 (2) | 0.0156 (2) | −0.00061 (16) | 0.00766 (18) | 0.00009 (15) |
C(4B) | 0.0161 (3) | 0.0176 (2) | 0.0164 (2) | 0.00151 (19) | 0.0090 (2) | 0.00284 (17) |
C(5B) | 0.0138 (3) | 0.0206 (3) | 0.0180 (3) | 0.0043 (2) | 0.0056 (2) | 0.00191 (19) |
O(1B) | 0.0118 (2) | 0.0216 (2) | 0.01631 (19) | 0.00528 (16) | 0.00614 (16) | 0.00637 (15) |
O(2B) | 0.0156 (3) | 0.0343 (4) | 0.01285 (19) | 0.0028 (2) | 0.00372 (18) | 0.00720 (19) |
O(3B) | 0.0170 (3) | 0.0265 (3) | 0.0243 (3) | 0.0020 (2) | 0.0120 (2) | 0.0102 (2) |
O(4B) | 0.0143 (3) | 0.0268 (3) | 0.0296 (4) | 0.0071 (2) | 0.0104 (2) | 0.0081 (3) |
O(5B) | 0.0203 (3) | 0.0246 (3) | 0.0197 (2) | 0.0083 (2) | 0.0059 (2) | 0.0088 (2) |
O(6B) | 0.0241 (3) | 0.0179 (2) | 0.0192 (2) | −0.00030 (19) | 0.0142 (2) | 0.00287 (16) |
O(7B) | 0.0217 (4) | 0.0312 (4) | 0.0267 (3) | 0.0112 (3) | 0.0169 (3) | 0.0089 (3) |
N(4B) | 0.0131 (2) | 0.01394 (18) | 0.01254 (17) | 0.00128 (13) | 0.00662 (15) | 0.00170 (12) |
N(5B) | 0.0118 (2) | 0.01402 (18) | 0.0171 (2) | 0.00268 (14) | 0.00331 (16) | 0.00226 (14) |
N(6B) | 0.0134 (2) | 0.0157 (2) | 0.01336 (18) | −0.00023 (14) | 0.00727 (16) | −0.00022 (13) |
C(6B) | 0.0099 (2) | 0.01176 (17) | 0.01155 (17) | 0.00073 (13) | 0.00464 (14) | 0.00097 (12) |
C(7B) | 0.0108 (2) | 0.01128 (17) | 0.01196 (17) | 0.00068 (13) | 0.00499 (14) | 0.00115 (12) |
C(8B) | 0.0111 (2) | 0.01180 (18) | 0.01421 (19) | 0.00099 (14) | 0.00569 (16) | 0.00085 (13) |
C(9B) | 0.0111 (2) | 0.01186 (18) | 0.01352 (19) | 0.00152 (13) | 0.00414 (16) | 0.00169 (13) |
C(10B) | 0.0122 (2) | 0.01257 (19) | 0.01226 (18) | 0.00087 (14) | 0.00470 (16) | 0.00161 (13) |
C(11B) | 0.0111 (2) | 0.01188 (17) | 0.01134 (17) | 0.00001 (13) | 0.00486 (15) | 0.00051 (12) |
O(8)—C(12) | 1.2575 (10) | C(13)—H(131) | 1.0830 (8) |
O(9)—C(12) | 1.2477 (12) | C(13)—H(132) | 1.0830 (7) |
O(1A)—C(6A) | 1.2461 (10) | C(14)—H(141) | 1.0830 (9) |
O(2A)—N(4A) | 1.2339 (12) | C(14)—H(142) | 1.0830 (11) |
O(3A)—N(4A) | 1.2271 (13) | C(14)—H(143) | 1.0830 (11) |
O(4A)—N(5A) | 1.2292 (17) | C(15)—H(151) | 1.0830 (11) |
O(5A)—N(5A) | 1.2355 (13) | C(15)—H(152) | 1.0830 (17) |
O(6A)—N(6A) | 1.2360 (11) | C(15)—H(153) | 1.0830 (11) |
O(7A)—N(6A) | 1.2206 (14) | C(16)—H(161) | 1.083 (2) |
O(1B)—C(6B) | 1.2427 (10) | C(16)—H(162) | 1.0830 (18) |
O(2B)—N(4B) | 1.2331 (12) | C(16)—H(163) | 1.0830 (13) |
O(3B)—N(4B) | 1.2236 (13) | C(2A)—H(2A) | 1.0830 (9) |
O(4B)—N(5B) | 1.2318 (16) | C(4A)—C(5A) | 1.3636 (15) |
O(5B)—N(5B) | 1.2399 (13) | C(4A)—H(4A) | 1.0830 (8) |
O(6B)—N(6B) | 1.2406 (11) | C(5A)—H(5A) | 1.0830 (11) |
O(7B)—N(6B) | 1.2225 (13) | C(6A)—C(7A) | 1.4522 (11) |
N(1A)—C(2A) | 1.3276 (14) | C(6A)—C(11A) | 1.4564 (8) |
N(1A)—C(5A) | 1.3750 (11) | C(7A)—C(8A) | 1.3857 (10) |
N(1A)—H(1A) | 1.0830 (6) | C(8A)—C(9A) | 1.3875 (9) |
N(3A)—C(2A) | 1.3329 (12) | C(8A)—H(8A) | 1.0830 (8) |
N(3A)—C(4A) | 1.3828 (15) | C(9A)—C(10A) | 1.3949 (12) |
N(3A)—H(3A) | 1.0830 (9) | C(10A)—C(11A) | 1.3687 (10) |
N(4A)—C(7A) | 1.4501 (8) | C(10A)—H(10A) | 1.0830 (6) |
N(5A)—C(9A) | 1.4458 (9) | C(2B)—H(2B) | 1.0830 (10) |
N(6A)—C(11A) | 1.4548 (11) | C(4B)—C(5B) | 1.3605 (13) |
N(1B)—C(2B) | 1.3288 (11) | C(4B)—H(4B) | 1.0830 (9) |
N(1B)—C(4B) | 1.3761 (14) | C(5B)—H(5B) | 1.0830 (10) |
N(1B)—H(1B) | 1.0830 (6) | C(6B)—C(7B) | 1.4620 (11) |
N(3B)—C(2B) | 1.3342 (12) | C(6B)—C(11B) | 1.4595 (9) |
N(3B)—C(5B) | 1.3770 (16) | C(7B)—C(8B) | 1.3760 (10) |
N(3B)—H(3B) | 1.0830 (7) | C(8B)—C(9B) | 1.3935 (10) |
N(4B)—C(7B) | 1.4576 (9) | C(8B)—H(8B) | 1.0830 (8) |
N(5B)—C(9B) | 1.4411 (10) | C(9B)—C(10B) | 1.3879 (12) |
N(6B)—C(11B) | 1.4536 (11) | C(10B)—C(11B) | 1.3797 (10) |
C(12)—C(13) | 1.5337 (10) | C(10B)—H(10B) | 1.0830 (7) |
C(2A)—N(1A)—C(5A) | 109.04 (7) | C(5A)—C(4A)—H(4A) | 131.39 (11) |
C(2A)—N(1A)—H(1A) | 122.13 (7) | N(1A)—C(5A)—C(4A) | 106.83 (9) |
C(5A)—N(1A)—H(1A) | 128.83 (9) | N(1A)—C(5A)—H(5A) | 122.22 (9) |
C(2A)—N(3A)—C(4A) | 108.44 (9) | C(4A)—C(5A)—H(5A) | 130.91 (8) |
C(2A)—N(3A)—H(3A) | 124.33 (9) | O(1A)—C(6A)—C(7A) | 126.40 (6) |
C(4A)—N(3A)—H(3A) | 127.01 (8) | O(1A)—C(6A)—C(11A) | 121.52 (7) |
O(2A)—N(4A)—O(3A) | 122.24 (7) | C(7A)—C(6A)—C(11A) | 112.05 (6) |
O(2A)—N(4A)—C(7A) | 119.49 (8) | N(4A)—C(7A)—C(6A) | 120.30 (6) |
O(3A)—N(4A)—C(7A) | 118.21 (7) | N(4A)—C(7A)—C(8A) | 115.97 (7) |
O(4A)—N(5A)—O(5A) | 123.94 (9) | C(6A)—C(7A)—C(8A) | 123.68 (6) |
O(4A)—N(5A)—C(9A) | 118.73 (8) | C(7A)—C(8A)—C(9A) | 119.39 (7) |
O(5A)—N(5A)—C(9A) | 117.32 (9) | C(7A)—C(8A)—H(8A) | 120.19 (6) |
O(6A)—N(6A)—O(7A) | 124.15 (10) | C(9A)—C(8A)—H(8A) | 120.40 (7) |
O(6A)—N(6A)—C(11A) | 117.29 (9) | N(5A)—C(9A)—C(8A) | 120.10 (7) |
O(7A)—N(6A)—C(11A) | 118.55 (7) | N(5A)—C(9A)—C(10A) | 118.60 (7) |
C(2B)—N(1B)—C(4B) | 108.90 (7) | C(8A)—C(9A)—C(10A) | 121.26 (6) |
C(2B)—N(1B)—H(1B) | 126.29 (8) | C(9A)—C(10A)—C(11A) | 118.80 (6) |
C(4B)—N(1B)—H(1B) | 124.75 (7) | C(9A)—C(10A)—H(10A) | 120.29 (7) |
C(2B)—N(3B)—C(5B) | 109.16 (7) | C(11A)—C(10A)—H(10A) | 120.86 (8) |
C(2B)—N(3B)—H(3B) | 125.10 (9) | N(6A)—C(11A)—C(6A) | 119.05 (6) |
C(5B)—N(3B)—H(3B) | 125.73 (9) | N(6A)—C(11A)—C(10A) | 116.15 (6) |
O(2B)—N(4B)—O(3B) | 122.97 (8) | C(6A)—C(11A)—C(10A) | 124.80 (7) |
O(2B)—N(4B)—C(7B) | 119.16 (8) | N(1B)—C(2B)—N(3B) | 108.26 (8) |
O(3B)—N(4B)—C(7B) | 117.87 (7) | N(1B)—C(2B)—H(2B) | 124.75 (8) |
O(4B)—N(5B)—O(5B) | 123.12 (9) | N(3B)—C(2B)—H(2B) | 126.97 (8) |
O(4B)—N(5B)—C(9B) | 118.81 (8) | N(1B)—C(4B)—C(5B) | 107.22 (8) |
O(5B)—N(5B)—C(9B) | 118.06 (10) | N(1B)—C(4B)—H(4B) | 120.80 (8) |
O(6B)—N(6B)—O(7B) | 122.88 (10) | C(5B)—C(4B)—H(4B) | 131.94 (11) |
O(6B)—N(6B)—C(11B) | 117.69 (8) | N(3B)—C(5B)—C(4B) | 106.46 (9) |
O(7B)—N(6B)—C(11B) | 119.41 (8) | N(3B)—C(5B)—H(5B) | 121.82 (9) |
O(8)—C(12)—O(9) | 126.25 (7) | C(4B)—C(5B)—H(5B) | 131.71 (11) |
O(8)—C(12)—C(13) | 113.39 (7) | O(1B)—C(6B)—C(7B) | 125.17 (7) |
O(9)—C(12)—C(13) | 120.34 (7) | O(1B)—C(6B)—C(11B) | 123.24 (8) |
C(12)—C(13)—H(131) | 106.59 (6) | C(7B)—C(6B)—C(11B) | 111.59 (6) |
C(12)—C(13)—H(132) | 107.67 (5) | N(4B)—C(7B)—C(6B) | 119.65 (6) |
H(131)—C(13)—H(132) | 111.63 (7) | N(4B)—C(7B)—C(8B) | 115.63 (7) |
H(141)—C(14)—H(142) | 112.44 (8) | C(6B)—C(7B)—C(8B) | 124.67 (6) |
H(141)—C(14)—H(143) | 110.22 (9) | C(7B)—C(8B)—C(9B) | 118.92 (8) |
H(142)—C(14)—H(143) | 111.74 (9) | C(7B)—C(8B)—H(8B) | 120.05 (7) |
H(151)—C(15)—H(152) | 114.56 (14) | C(9B)—C(8B)—H(8B) | 121.03 (7) |
H(151)—C(15)—H(153) | 108.70 (10) | N(5B)—C(9B)—C(8B) | 119.94 (8) |
H(152)—C(15)—H(153) | 112.02 (10) | N(5B)—C(9B)—C(10B) | 118.98 (7) |
H(161)—C(16)—H(162) | 111.45 (12) | C(8B)—C(9B)—C(10B) | 121.08 (7) |
H(161)—C(16)—H(163) | 113.16 (17) | C(9B)—C(10B)—C(11B) | 119.73 (6) |
H(162)—C(16)—H(163) | 111.22 (13) | C(9B)—C(10B)—H(10B) | 119.74 (7) |
N(1A)—C(2A)—N(3A) | 108.81 (8) | C(11B)—C(10B)—H(10B) | 120.51 (8) |
N(1A)—C(2A)—H(2A) | 126.99 (8) | N(6B)—C(11B)—C(6B) | 120.17 (6) |
N(3A)—C(2A)—H(2A) | 124.17 (10) | N(6B)—C(11B)—C(10B) | 115.94 (6) |
N(3A)—C(4A)—C(5A) | 106.88 (7) | C(6B)—C(11B)—C(10B) | 123.85 (7) |
N(3A)—C(4A)—H(4A) | 121.72 (10) |
Experimental details
(Rubrene_neutron) | (Rubrene_Xray_multipolemodel) | (Rubrene_Xray_MM_Shade) | (Rubrene_Xray_IAM) | |
Crystal data | ||||
Chemical formula | C42H28 | C42H28 | C42H28 | C42H28 |
Mr | 532.69 | 532.69 | 532.64 | 532.69 |
Crystal system, space group | Orthorhombic, Cmca | Orthorhombic, Cmca | Orthorhombic, Cmca | Orthorhombic, Cmca |
Temperature (K) | 100 | 100 | 100 | 100 |
a, b, c (Å) | 26.7972 (3), 7.1617 (1), 14.1940 (2) | 26.8106 (3), 7.1602 (1), 14.2029 (1) | 26.8106 (3), 7.1602 (1), 14.2029 (1) | 26.8106 (3), 7.1602 (1), 14.2029 (1) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 90, 90 | 90, 90, 90 |
V (Å3) | 2724.01 (5) | 2726.52 (5) | 2726.52 (5) | 2726.52 (5) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Neutron, λ = 0.4-3.4 Å | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.20 | 0.07 | 0.07 | 0.07 |
Crystal size (mm) | 1.50 × 1.50 × 1.00 | 0.24 × 0.22 × 0.18 | 0.24 × 0.22 × 0.18 | 0.24 × 0.22 × 0.18 |
Data collection | ||||
Diffractometer | TOPAZ Single Crystal Diffractometer | SuperNova, Single source at offset, Atlas diffractometer | SuperNova, Single source at offset, Atlas diffractometer | SuperNova, Single source at offset, Atlas diffractometer |
Absorption correction | Analytical The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 1.189 + 0.789 * lambda [cm-1] The value of 1.978(cm-1)given in _exptl_absorpt_coefficient_mu is the value at 1 Å | Analytical | Analytical | Analytical |
Tmin, Tmax | 0.646, 0.848 | 0.983, 0.987 | 0.983, 0.987 | 0.983, 0.987 |
No. of measured, independent and observed [ > 3σ(I)] reflections | 24945, 22955, 22955 | 83536, 7703, 6070 | 83536, 7703, 6070 | 83536, 7703, 6070 |
Rint | ? | 0.033 | 0.033 | 0.033 |
Distance from source to specimen (mm) | – | 1.100 | 1.100 | 1.100 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.055, 1.57 | 0.022, 0.055, 1.49 | 0.022, 0.055, 1.49 | 0.047, 0.135, 3.55 |
No. of reflections | 22775 | 6070 | 6070 | 6070 |
No. of parameters | 182 | 383 | 383 | 96 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | All H-atom parameters refined | ? | The heavy atoms from the multipole refinement was used to calculate anisotropic
hydrogen thermal parameters using the SHADE2.1 server SHADE web server for estimation of hydrogen anisotropic displacement parameters. Anders Østergaard Madsen. J. Appl. Cryst. 39, 757-758 www.shade.ki.ku.dk | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.31 | 0.18, −0.18 | 0.18, −0.18 | 0.76, −0.26 |
(Rubrene_Xray_IAM_HO) | (Rubrene_HAR) | (BIPa_neutron_100K) | (BIPa_X_multipole_model) | |
Crystal data | ||||
Chemical formula | C42H28 | C42H28 | 2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | 2(C6H2N3O7)·C5H11NO2·2(C3H5N2) |
Mr | 532.69 | 532.69 | 711.51 | 711.51 |
Crystal system, space group | Orthorhombic, Cmca | Orthorhombic, Cmca | Monoclinic, C2/c | Monoclinic, C2/c |
Temperature (K) | 100 | 100 | 100 | 100 |
a, b, c (Å) | 26.8106 (3), 7.1602 (1), 14.2029 (1) | 26.8106 (3), 7.1602 (1), 14.2029 (1) | 33.5759 (1), 7.6607 (1), 25.1114 (2) | 33.5939 (5), 7.66580 (8), 25.1324 (3) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 114.6982 (4), 90 | 90, 114.7162 (17), 90 |
V (Å3) | 2726.52 (5) | 2726.52 (5) | 5868.14 (7) | 5879.29 (13) |
Z | 4 | 4 | 8 | 8 |
Radiation type | Mo Kα | Mo Kα | Neutron, λ = 0.4-3.4 Å | Mo Kα |
µ (mm−1) | 0.07 | 0.07 | 0.19 | 0.14 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 | 0.24 × 0.22 × 0.18 | 0.6 (radius) | 0.29 × 0.21 × 0.16 |
Data collection | ||||
Diffractometer | SuperNova, Single source at offset, Atlas diffractometer | SuperNova, Single source at offset, Atlas diffractometer | TOPAZ Single Crystal Diffractometer | SuperNova, Single source at offset, Atlas diffractometer |
Absorption correction | Analytical | Analytical | Analytical The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 1.220 + 0.639 * lambda [cm-1] The value of 1.859(cm-1)given in _exptl_absorpt_coefficient_mu is the value at 1 Å | Gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model |
Tmin, Tmax | 0.983, 0.987 | 0.983, 0.987 | 0.747, 0.888 | 0.974, 0.982 |
No. of measured, independent and observed [ > 3σ(I)] reflections | 83536, 7703, 6070 | 83536, 7703, 6070 | 32750, 25886, 25886 | 165808, 27262, 21277 |
Rint | 0.033 | 0.033 | ? | 0.035 |
Distance from source to specimen (mm) | 1.100 | 1.100 | – | 1.201 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.068, 1.31 | ?, 0.033, 2.96 | 0.051, 0.040, 1.57 | 0.03, 0.072, 0.87 |
No. of reflections | 3336 | 6289 | 25886 | 21277 |
No. of parameters | 96 | 159 | 693 | 1306 |
No. of restraints | 0 | 0 | 0 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | All H-atom parameters refined | All H-atom parameters refined | ? |
Δρmax, Δρmin (e Å−3) | 0.10, −0.11 | ?, ? | 0.21, −0.20 | 0.31, −0.26 |
(BIPa_X_MM_Shade) | (BIPa_Xray_IAM) | (BIPa_X_HO_IAM) | |
Crystal data | |||
Chemical formula | 2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | 2(C6H2N3O7)·C5H11NO2·2(C3H5N2) | 2(C6H2N3O7)·C5H11NO2·2(C3H5N2) |
Mr | 711.51 | 711.51 | 711.51 |
Crystal system, space group | Monoclinic, C2/c | Monoclinic, C2/c | Monoclinic, C2/c |
Temperature (K) | 100 | 100 | 100 |
a, b, c (Å) | 33.5939 (5), 7.66580 (8), 25.1324 (3) | 33.5939 (5), 7.66580 (8), 25.1324 (3) | 33.5939 (5), 7.66580 (8), 25.1324 (3) |
α, β, γ (°) | 90, 114.7162 (17), 90 | 90, 114.7162 (17), 90 | 90, 114.7162 (17), 90 |
V (Å3) | 5879.29 (13) | 5879.29 (13) | 5879.29 (13) |
Z | 8 | 8 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.14 | 0.14 | 0.14 |
Crystal size (mm) | 0.29 × 0.21 × 0.16 | 0.29 × 0.21 × 0.16 | 0.29 × 0.21 × 0.16 |
Data collection | |||
Diffractometer | SuperNova, Single source at offset, Atlas diffractometer | SuperNova, Single source at offset, Atlas diffractometer | SuperNova, Single source at offset, Atlas diffractometer |
Absorption correction | Gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | Gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model | Gaussian CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model |
Tmin, Tmax | 0.974, 0.982 | 0.974, 0.982 | 0.974, 0.982 |
No. of measured, independent and observed [ > 3σ(I)] reflections | 165808, 27262, 21277 | 165808, 27262, 21277 | 165808, 27262, 21277 |
Rint | 0.035 | 0.035 | 0.035 |
Distance from source to specimen (mm) | 1.201 | 1.201 | 1.201 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.03, 0.072, 0.87 | 0.051, 0.127, 1.51 | 0.056, 0.166, 0.8 |
No. of reflections | 21277 | 21277 | 10569 |
No. of parameters | 1306 | 451 | 451 |
No. of restraints | 1 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | ? | ? |
Δρmax, Δρmin (e Å−3) | 0.31, −0.26 | 0.90, −0.41 | 0.19, −0.21 |
Computer programs: CrystalPlan (Zikovsky, J. et al. 2011), CrysAlis PRO, Agilent Technologies Version 1.171.36.28, CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44), MANTID (Taylor, J. et al. 2012) & ANVRED2X (local program), SHELXS97 (Sheldrick, 2008), GSAS (Larson & Von Dreele, 2004), SHELXL97 (Sheldrick, 2008), Volkov et al., (2006), XD2006 (Volkov et al., 2006).
C(1)—C(1)i | 1.4644 (5) | C(6)—C(7) | 1.3978 (3) |
C(1)—C(1)ii | 1.4644 (5) | C(6)—C(11) | 1.3981 (3) |
C(1)—C(2) | 1.4263 (2) | C(7)—C(8) | 1.3917 (3) |
C(1)—C(2)iii | 1.4263 (2) | C(7)—H(7) | 1.0900 (3) |
C(2)—C(3) | 1.4065 (3) | C(8)—C(9) | 1.3933 (4) |
C(2)—C(6) | 1.4972 (3) | C(8)—H(8) | 1.0900 (3) |
C(3)—C(3)i | 1.4394 (4) | C(9)—C(10) | 1.3950 (4) |
C(3)—C(4) | 1.4371 (3) | C(9)—H(9) | 1.0900 (3) |
C(4)—C(5) | 1.3658 (3) | C(10)—C(11) | 1.3967 (3) |
C(4)—H(4) | 1.0900 (2) | C(10)—H(10) | 1.0900 (3) |
C(5)—C(5)i | 1.4229 (5) | C(11)—H(11) | 1.0900 (2) |
C(5)—H(5) | 1.0900 (2) | ||
C(1)i—C(1)—C(2) | 119.135 (12) | C(2)—C(6)—C(7) | 122.05 (2) |
C(1)i—C(1)—C(2)iii | 119.135 (12) | C(2)—C(6)—C(11) | 118.992 (19) |
C(1)ii—C(1)—C(2) | 119.135 (12) | C(7)—C(6)—C(11) | 118.56 (2) |
C(1)ii—C(1)—C(2)iii | 119.135 (12) | C(6)—C(7)—C(8) | 120.68 (2) |
C(2)—C(1)—C(2)iii | 121.73 (2) | C(6)—C(7)—H(7) | 119.60 (2) |
C(1)—C(2)—C(3) | 120.312 (18) | C(8)—C(7)—H(7) | 119.71 (2) |
C(1)—C(2)—C(6) | 123.334 (19) | C(7)—C(8)—C(9) | 120.46 (3) |
C(1)iii—C(2)—C(3) | 120.312 (18) | C(7)—C(8)—H(8) | 118.76 (3) |
C(1)iii—C(2)—C(6) | 123.334 (19) | C(9)—C(8)—H(8) | 120.78 (3) |
C(3)—C(2)—C(6) | 115.937 (18) | C(8)—C(9)—C(10) | 119.44 (3) |
C(2)—C(3)—C(3)i | 120.173 (11) | C(8)—C(9)—H(9) | 119.77 (3) |
C(2)—C(3)—C(4) | 121.546 (19) | C(10)—C(9)—H(9) | 120.80 (3) |
C(3)i—C(3)—C(4) | 118.127 (12) | C(9)—C(10)—C(11) | 119.93 (3) |
C(3)—C(4)—C(5) | 121.72 (2) | C(9)—C(10)—H(10) | 121.12 (3) |
C(3)—C(4)—H(4) | 118.18 (2) | C(11)—C(10)—H(10) | 118.94 (3) |
C(5)—C(4)—H(4) | 120.10 (2) | C(6)—C(11)—C(10) | 120.92 (2) |
C(4)—C(5)—C(5)i | 120.137 (14) | C(6)—C(11)—H(11) | 119.02 (2) |
C(4)—C(5)—H(5) | 119.97 (2) | C(10)—C(11)—H(11) | 120.05 (2) |
C(5)i—C(5)—H(5) | 119.815 (13) | ||
C(1)i—C(1)—C(2)—C(3) | 7.063 (16) | C(2)—C(6)—C(7)—C(8) | −172.57 (3) |
C(1)i—C(1)—C(2)—C(6) | −165.22 (3) | C(2)—C(6)—C(7)—H(7) | 8.252 (19) |
C(1)ii—C(1)—C(2)—C(3) | 7.063 (16) | C(2)—C(6)—C(11)—C(10) | 173.55 (3) |
C(1)ii—C(1)—C(2)—C(6) | −165.22 (3) | C(2)—C(6)—C(11)—H(11) | −6.79 (2) |
C(2)iii—C(1)—C(2)—C(3) | −172.94 (3) | C(11)—C(6)—C(7)—C(8) | 0.15 (2) |
C(2)iii—C(1)—C(2)—C(6) | 14.776 (18) | C(7)—C(6)—C(11)—C(10) | 0.60 (2) |
C(1)—C(2)—C(3)—C(4) | 177.45 (3) | C(11)—C(6)—C(7)—H(7) | −179.02 (3) |
C(1)—C(2)—C(6)—C(7) | −110.10 (3) | C(7)—C(6)—C(11)—H(11) | −179.74 (3) |
C(1)—C(2)—C(6)—C(11) | 77.21 (2) | C(6)—C(7)—C(8)—C(9) | −0.71 (3) |
C(1)iii—C(2)—C(3)—C(4) | 177.45 (3) | C(6)—C(7)—C(8)—H(8) | 179.47 (4) |
C(1)iii—C(2)—C(6)—C(7) | −110.10 (3) | H(7)—C(7)—C(8)—C(9) | 178.47 (4) |
C(1)iii—C(2)—C(6)—C(11) | 77.21 (2) | H(7)—C(7)—C(8)—H(8) | −1.35 (2) |
C(6)—C(2)—C(3)—C(4) | −9.713 (19) | C(7)—C(8)—C(9)—C(10) | 0.52 (3) |
C(3)—C(2)—C(6)—C(7) | 77.30 (2) | C(7)—C(8)—C(9)—H(9) | −179.72 (5) |
C(3)—C(2)—C(6)—C(11) | −95.39 (2) | H(8)—C(8)—C(9)—C(10) | −179.67 (5) |
C(3)i—C(3)—C(2)—C(1) | −7.136 (17) | H(8)—C(8)—C(9)—H(9) | 0.09 (3) |
C(3)i—C(3)—C(2)—C(6) | 165.70 (3) | C(8)—C(9)—C(10)—C(11) | 0.23 (3) |
C(2)—C(3)—C(4)—C(5) | 176.84 (3) | C(8)—C(9)—C(10)—H(10) | −179.03 (5) |
C(2)—C(3)—C(4)—H(4) | −3.493 (19) | H(9)—C(9)—C(10)—C(11) | −179.53 (5) |
C(3)i—C(3)—C(4)—C(5) | 1.33 (2) | H(9)—C(9)—C(10)—H(10) | 1.21 (3) |
C(3)i—C(3)—C(4)—H(4) | −179.00 (3) | C(9)—C(10)—C(11)—C(6) | −0.79 (3) |
C(3)—C(4)—C(5)—H(5) | −178.19 (4) | C(9)—C(10)—C(11)—H(11) | 179.55 (4) |
H(4)—C(4)—C(5)—H(5) | 2.14 (2) | H(10)—C(10)—C(11)—C(6) | 178.48 (4) |
C(5)i—C(5)—C(4)—C(3) | −1.36 (2) | H(10)—C(10)—C(11)—H(11) | −1.18 (2) |
C(5)i—C(5)—C(4)—H(4) | 178.98 (4) |
Symmetry codes: (i) −x, y, z; (ii) −x, −y, −z; (iii) x, −y, −z. |
C(1)—C(1)i | 1.4644 (5) | C(6)—C(7) | 1.3978 (3) |
C(1)—C(1)ii | 1.4644 (5) | C(6)—C(11) | 1.3981 (3) |
C(1)—C(2) | 1.4263 (2) | C(7)—C(8) | 1.3917 (3) |
C(1)—C(2)iii | 1.4263 (2) | C(7)—H(7) | 1.0900 (3) |
C(2)—C(3) | 1.4065 (3) | C(8)—C(9) | 1.3933 (4) |
C(2)—C(6) | 1.4972 (3) | C(8)—H(8) | 1.0900 (3) |
C(3)—C(3)i | 1.4394 (4) | C(9)—C(10) | 1.3950 (4) |
C(3)—C(4) | 1.4371 (3) | C(9)—H(9) | 1.0900 (3) |
C(4)—C(5) | 1.3658 (3) | C(10)—C(11) | 1.3967 (3) |
C(4)—H(4) | 1.0900 (2) | C(10)—H(10) | 1.0900 (3) |
C(5)—C(5)i | 1.4229 (5) | C(11)—H(11) | 1.0900 (2) |
C(5)—H(5) | 1.0900 (2) | ||
C(1)i—C(1)—C(2) | 119.135 (12) | C(2)—C(6)—C(7) | 122.05 (2) |
C(1)i—C(1)—C(2)iii | 119.135 (12) | C(2)—C(6)—C(11) | 118.992 (19) |
C(1)ii—C(1)—C(2) | 119.135 (12) | C(7)—C(6)—C(11) | 118.56 (2) |
C(1)ii—C(1)—C(2)iii | 119.135 (12) | C(6)—C(7)—C(8) | 120.68 (2) |
C(2)—C(1)—C(2)iii | 121.73 (2) | C(6)—C(7)—H(7) | 119.60 (2) |
C(1)—C(2)—C(3) | 120.312 (18) | C(8)—C(7)—H(7) | 119.71 (2) |
C(1)—C(2)—C(6) | 123.334 (19) | C(7)—C(8)—C(9) | 120.46 (3) |
C(1)iii—C(2)—C(3) | 120.312 (18) | C(7)—C(8)—H(8) | 118.76 (3) |
C(1)iii—C(2)—C(6) | 123.334 (19) | C(9)—C(8)—H(8) | 120.78 (3) |
C(3)—C(2)—C(6) | 115.937 (18) | C(8)—C(9)—C(10) | 119.44 (3) |
C(2)—C(3)—C(3)i | 120.173 (11) | C(8)—C(9)—H(9) | 119.77 (3) |
C(2)—C(3)—C(4) | 121.546 (19) | C(10)—C(9)—H(9) | 120.80 (3) |
C(3)i—C(3)—C(4) | 118.127 (12) | C(9)—C(10)—C(11) | 119.93 (3) |
C(3)—C(4)—C(5) | 121.72 (2) | C(9)—C(10)—H(10) | 121.12 (3) |
C(3)—C(4)—H(4) | 118.18 (2) | C(11)—C(10)—H(10) | 118.94 (3) |
C(5)—C(4)—H(4) | 120.10 (2) | C(6)—C(11)—C(10) | 120.92 (2) |
C(4)—C(5)—C(5)i | 120.137 (14) | C(6)—C(11)—H(11) | 119.02 (2) |
C(4)—C(5)—H(5) | 119.97 (2) | C(10)—C(11)—H(11) | 120.05 (2) |
C(5)i—C(5)—H(5) | 119.815 (13) | ||
C(1)i—C(1)—C(2)—C(3) | 7.063 (16) | C(2)—C(6)—C(7)—C(8) | −172.57 (3) |
C(1)i—C(1)—C(2)—C(6) | −165.22 (3) | C(2)—C(6)—C(7)—H(7) | 8.252 (19) |
C(1)ii—C(1)—C(2)—C(3) | 7.063 (16) | C(2)—C(6)—C(11)—C(10) | 173.55 (3) |
C(1)ii—C(1)—C(2)—C(6) | −165.22 (3) | C(2)—C(6)—C(11)—H(11) | −6.79 (2) |
C(2)iii—C(1)—C(2)—C(3) | −172.94 (3) | C(11)—C(6)—C(7)—C(8) | 0.15 (2) |
C(2)iii—C(1)—C(2)—C(6) | 14.776 (18) | C(7)—C(6)—C(11)—C(10) | 0.60 (2) |
C(1)—C(2)—C(3)—C(4) | 177.45 (3) | C(11)—C(6)—C(7)—H(7) | −179.02 (3) |
C(1)—C(2)—C(6)—C(7) | −110.10 (3) | C(7)—C(6)—C(11)—H(11) | −179.74 (3) |
C(1)—C(2)—C(6)—C(11) | 77.21 (2) | C(6)—C(7)—C(8)—C(9) | −0.71 (3) |
C(1)iii—C(2)—C(3)—C(4) | 177.45 (3) | C(6)—C(7)—C(8)—H(8) | 179.47 (4) |
C(1)iii—C(2)—C(6)—C(7) | −110.10 (3) | H(7)—C(7)—C(8)—C(9) | 178.47 (4) |
C(1)iii—C(2)—C(6)—C(11) | 77.21 (2) | H(7)—C(7)—C(8)—H(8) | −1.35 (2) |
C(6)—C(2)—C(3)—C(4) | −9.713 (19) | C(7)—C(8)—C(9)—C(10) | 0.52 (3) |
C(3)—C(2)—C(6)—C(7) | 77.30 (2) | C(7)—C(8)—C(9)—H(9) | −179.72 (5) |
C(3)—C(2)—C(6)—C(11) | −95.39 (2) | H(8)—C(8)—C(9)—C(10) | −179.67 (5) |
C(3)i—C(3)—C(2)—C(1) | −7.136 (17) | H(8)—C(8)—C(9)—H(9) | 0.09 (3) |
C(3)i—C(3)—C(2)—C(6) | 165.70 (3) | C(8)—C(9)—C(10)—C(11) | 0.23 (3) |
C(2)—C(3)—C(4)—C(5) | 176.84 (3) | C(8)—C(9)—C(10)—H(10) | −179.03 (5) |
C(2)—C(3)—C(4)—H(4) | −3.493 (19) | H(9)—C(9)—C(10)—C(11) | −179.53 (5) |
C(3)i—C(3)—C(4)—C(5) | 1.33 (2) | H(9)—C(9)—C(10)—H(10) | 1.21 (3) |
C(3)i—C(3)—C(4)—H(4) | −179.00 (3) | C(9)—C(10)—C(11)—C(6) | −0.79 (3) |
C(3)—C(4)—C(5)—H(5) | −178.19 (4) | C(9)—C(10)—C(11)—H(11) | 179.55 (4) |
H(4)—C(4)—C(5)—H(5) | 2.14 (2) | H(10)—C(10)—C(11)—C(6) | 178.48 (4) |
C(5)i—C(5)—C(4)—C(3) | −1.36 (2) | H(10)—C(10)—C(11)—H(11) | −1.18 (2) |
C(5)i—C(5)—C(4)—H(4) | 178.98 (4) |
Symmetry codes: (i) −x, y, z; (ii) −x, −y, −z; (iii) x, −y, −z. |
C(1)—C(1)i | 1.4631 (10) | C(6)—C(7) | 1.3985 (6) |
C(1)—C(1)ii | 1.4631 (10) | C(6)—C(11) | 1.3965 (7) |
C(1)—C(2) | 1.4270 (5) | C(7)—C(8) | 1.3945 (7) |
C(1)—C(2)iii | 1.4270 (5) | C(7)—H(7) | 1.0862 (5) |
C(2)—C(3) | 1.4056 (6) | C(8)—C(9) | 1.3892 (9) |
C(2)—C(6) | 1.4983 (6) | C(8)—H(8) | 1.0855 (5) |
C(3)—C(3)i | 1.4412 (8) | C(9)—C(10) | 1.3926 (8) |
C(3)—C(4) | 1.4375 (6) | C(9)—H(9) | 1.0858 (5) |
C(4)—C(5) | 1.3648 (7) | C(10)—C(11) | 1.3953 (7) |
C(4)—H(4) | 1.0839 (5) | C(10)—H(10) | 1.0863 (6) |
C(5)—C(5)i | 1.4206 (10) | C(11)—H(11) | 1.0837 (5) |
C(5)—H(5) | 1.0875 (5) | ||
C(1)i—C(1)—C(2) | 119.14 (2) | C(2)—C(6)—C(7) | 122.02 (4) |
C(1)i—C(1)—C(2)iii | 119.14 (2) | C(2)—C(6)—C(11) | 118.93 (4) |
C(1)ii—C(1)—C(2) | 119.14 (2) | C(7)—C(6)—C(11) | 118.66 (4) |
C(1)ii—C(1)—C(2)iii | 119.14 (2) | C(6)—C(7)—C(8) | 120.45 (5) |
C(2)—C(1)—C(2)iii | 121.73 (5) | C(6)—C(7)—H(7) | 119.56 (4) |
C(1)—C(2)—C(3) | 120.33 (4) | C(8)—C(7)—H(7) | 119.99 (4) |
C(1)—C(2)—C(6) | 123.34 (4) | C(7)—C(8)—C(9) | 120.42 (5) |
C(1)iii—C(2)—C(3) | 120.33 (4) | C(7)—C(8)—H(8) | 118.68 (5) |
C(1)iii—C(2)—C(6) | 123.34 (4) | C(9)—C(8)—H(8) | 120.91 (5) |
C(3)—C(2)—C(6) | 115.93 (3) | C(8)—C(9)—C(10) | 119.68 (4) |
C(2)—C(3)—C(3)i | 120.14 (2) | C(8)—C(9)—H(9) | 119.45 (5) |
C(2)—C(3)—C(4) | 121.65 (4) | C(10)—C(9)—H(9) | 120.87 (5) |
C(3)i—C(3)—C(4) | 118.05 (2) | C(9)—C(10)—C(11) | 119.85 (5) |
C(3)—C(4)—C(5) | 121.75 (4) | C(9)—C(10)—H(10) | 120.93 (5) |
C(3)—C(4)—H(4) | 118.10 (4) | C(11)—C(10)—H(10) | 119.21 (5) |
C(5)—C(4)—H(4) | 120.15 (4) | C(6)—C(11)—C(10) | 120.94 (5) |
C(4)—C(5)—C(5)i | 120.19 (3) | C(6)—C(11)—H(11) | 119.04 (4) |
C(4)—C(5)—H(5) | 119.87 (4) | C(10)—C(11)—H(11) | 120.02 (5) |
C(5)i—C(5)—H(5) | 119.86 (3) |
Symmetry codes: (i) −x, y, z; (ii) −x, −y, −z; (iii) x, −y, −z. |
C(1)—C(1)i | 1.4654 (7) | C(6)—C(7) | 1.3982 (4) |
C(1)—C(1)ii | 1.4654 (7) | C(6)—C(11) | 1.3980 (5) |
C(1)—C(2) | 1.4257 (3) | C(7)—C(8) | 1.3929 (5) |
C(1)—C(2)iii | 1.4257 (3) | C(7)—H(7) | 1.0862 (4) |
C(2)—C(3) | 1.4064 (4) | C(8)—C(9) | 1.3927 (8) |
C(2)—C(6) | 1.4979 (4) | C(8)—H(8) | 1.0855 (4) |
C(3)—C(3)i | 1.4398 (5) | C(9)—C(10) | 1.3934 (8) |
C(3)—C(4) | 1.4376 (4) | C(9)—H(9) | 1.0858 (4) |
C(4)—C(5) | 1.3658 (5) | C(10)—C(11) | 1.3970 (5) |
C(4)—H(4) | 1.0839 (3) | C(10)—H(10) | 1.0863 (5) |
C(5)—C(5)i | 1.4220 (8) | C(11)—H(11) | 1.0837 (4) |
C(5)—H(5) | 1.0875 (3) | ||
C(1)i—C(1)—C(2) | 119.114 (16) | C(2)—C(6)—C(7) | 122.01 (3) |
C(1)i—C(1)—C(2)iii | 119.114 (16) | C(2)—C(6)—C(11) | 119.03 (3) |
C(1)ii—C(1)—C(2) | 119.114 (16) | C(7)—C(6)—C(11) | 118.57 (3) |
C(1)ii—C(1)—C(2)iii | 119.114 (16) | C(6)—C(7)—C(8) | 120.63 (4) |
C(2)—C(1)—C(2)iii | 121.77 (3) | C(6)—C(7)—H(7) | 119.53 (3) |
C(1)—C(2)—C(3) | 120.36 (2) | C(8)—C(7)—H(7) | 119.83 (3) |
C(1)—C(2)—C(6) | 123.32 (3) | C(7)—C(8)—C(9) | 120.45 (4) |
C(1)iii—C(2)—C(3) | 120.36 (2) | C(7)—C(8)—H(8) | 118.95 (4) |
C(1)iii—C(2)—C(6) | 123.32 (3) | C(9)—C(8)—H(8) | 120.60 (4) |
C(3)—C(2)—C(6) | 115.89 (2) | C(8)—C(9)—C(10) | 119.46 (3) |
C(2)—C(3)—C(3)i | 120.152 (15) | C(8)—C(9)—H(9) | 119.71 (5) |
C(2)—C(3)—C(4) | 121.56 (2) | C(10)—C(9)—H(9) | 120.83 (5) |
C(3)i—C(3)—C(4) | 118.134 (17) | C(9)—C(10)—C(11) | 119.99 (4) |
C(3)—C(4)—C(5) | 121.67 (3) | C(9)—C(10)—H(10) | 121.04 (4) |
C(3)—C(4)—H(4) | 118.23 (3) | C(11)—C(10)—H(10) | 118.96 (5) |
C(5)—C(4)—H(4) | 120.10 (3) | C(6)—C(11)—C(10) | 120.89 (4) |
C(4)—C(5)—C(5)i | 120.186 (19) | C(6)—C(11)—H(11) | 118.95 (3) |
C(4)—C(5)—H(5) | 119.90 (3) | C(10)—C(11)—H(11) | 120.16 (4) |
C(5)i—C(5)—H(5) | 119.83 (2) |
Symmetry codes: (i) −x, y, z; (ii) −x, −y, −z; (iii) x, −y, −z. |
O(8)—C(12) | 1.2582 (7) | C(13)—H(131) | 1.0830 (4) |
O(9)—C(12) | 1.2461 (8) | C(13)—H(132) | 1.0830 (4) |
O(1A)—C(6A) | 1.2455 (7) | C(14)—H(141) | 1.0830 (5) |
O(2A)—N(4A) | 1.2329 (9) | C(14)—H(142) | 1.0830 (5) |
O(3A)—N(4A) | 1.2265 (9) | C(14)—H(143) | 1.0830 (5) |
O(4A)—N(5A) | 1.2283 (11) | C(15)—H(151) | 1.0830 (6) |
O(5A)—N(5A) | 1.2354 (9) | C(15)—H(152) | 1.0830 (7) |
O(6A)—N(6A) | 1.2353 (8) | C(15)—H(153) | 1.0830 (6) |
O(7A)—N(6A) | 1.2212 (9) | C(16)—H(161) | 1.0830 (8) |
O(1B)—C(6B) | 1.2429 (7) | C(16)—H(162) | 1.0830 (7) |
O(2B)—N(4B) | 1.2318 (8) | C(16)—H(163) | 1.0830 (6) |
O(3B)—N(4B) | 1.2251 (9) | C(2A)—H(2A) | 1.0830 (5) |
O(4B)—N(5B) | 1.2318 (11) | C(4A)—C(5A) | 1.3631 (7) |
O(5B)—N(5B) | 1.2392 (9) | C(4A)—H(4A) | 1.0830 (5) |
O(6B)—N(6B) | 1.2409 (8) | C(5A)—H(5A) | 1.0830 (6) |
O(7B)—N(6B) | 1.2246 (9) | C(6A)—C(7A) | 1.4529 (6) |
N(1A)—C(2A) | 1.3290 (7) | C(6A)—C(11A) | 1.4544 (5) |
N(1A)—C(5A) | 1.3743 (6) | C(7A)—C(8A) | 1.3864 (5) |
N(1A)—H(1A) | 1.0830 (4) | C(8A)—C(9A) | 1.3861 (5) |
N(3A)—C(2A) | 1.3330 (6) | C(8A)—H(8A) | 1.0830 (4) |
N(3A)—C(4A) | 1.3808 (7) | C(9A)—C(10A) | 1.3933 (6) |
N(3A)—H(3A) | 1.0830 (5) | C(10A)—C(11A) | 1.3706 (5) |
N(4A)—C(7A) | 1.4490 (5) | C(10A)—H(10A) | 1.0830 (4) |
N(5A)—C(9A) | 1.4460 (6) | C(2B)—H(2B) | 1.0830 (5) |
N(6A)—C(11A) | 1.4549 (6) | C(4B)—C(5B) | 1.3613 (6) |
N(1B)—C(2B) | 1.3293 (6) | C(4B)—H(4B) | 1.0830 (5) |
N(1B)—C(4B) | 1.3767 (7) | C(5B)—H(5B) | 1.0830 (5) |
N(1B)—H(1B) | 1.0830 (4) | C(6B)—C(7B) | 1.4601 (6) |
N(3B)—C(2B) | 1.3349 (6) | C(6B)—C(11B) | 1.4598 (5) |
N(3B)—C(5B) | 1.3784 (7) | C(7B)—C(8B) | 1.3785 (5) |
N(3B)—H(3B) | 1.0830 (4) | C(8B)—C(9B) | 1.3940 (6) |
N(4B)—C(7B) | 1.4553 (5) | C(8B)—H(8B) | 1.0830 (5) |
N(5B)—C(9B) | 1.4408 (6) | C(9B)—C(10B) | 1.3883 (6) |
N(6B)—C(11B) | 1.4537 (6) | C(10B)—C(11B) | 1.3796 (6) |
C(12)—C(13) | 1.5322 (5) | C(10B)—H(10B) | 1.0830 (4) |
C(2A)—N(1A)—C(5A) | 108.97 (4) | C(5A)—C(4A)—H(4A) | 131.15 (5) |
C(2A)—N(1A)—H(1A) | 122.03 (4) | N(1A)—C(5A)—C(4A) | 106.88 (5) |
C(5A)—N(1A)—H(1A) | 129.00 (5) | N(1A)—C(5A)—H(5A) | 122.06 (5) |
C(2A)—N(3A)—C(4A) | 108.50 (5) | C(4A)—C(5A)—H(5A) | 131.03 (5) |
C(2A)—N(3A)—H(3A) | 124.41 (5) | O(1A)—C(6A)—C(7A) | 126.20 (4) |
C(4A)—N(3A)—H(3A) | 126.86 (4) | O(1A)—C(6A)—C(11A) | 121.61 (5) |
O(2A)—N(4A)—O(3A) | 122.13 (6) | C(7A)—C(6A)—C(11A) | 112.14 (3) |
O(2A)—N(4A)—C(7A) | 119.52 (5) | N(4A)—C(7A)—C(6A) | 120.43 (4) |
O(3A)—N(4A)—C(7A) | 118.28 (5) | N(4A)—C(7A)—C(8A) | 116.00 (4) |
O(4A)—N(5A)—O(5A) | 123.94 (7) | C(6A)—C(7A)—C(8A) | 123.52 (3) |
O(4A)—N(5A)—C(9A) | 118.70 (6) | C(7A)—C(8A)—C(9A) | 119.52 (4) |
O(5A)—N(5A)—C(9A) | 117.36 (6) | C(7A)—C(8A)—H(8A) | 120.09 (4) |
O(6A)—N(6A)—O(7A) | 124.13 (7) | C(9A)—C(8A)—H(8A) | 120.37 (4) |
O(6A)—N(6A)—C(11A) | 117.38 (6) | N(5A)—C(9A)—C(8A) | 120.17 (4) |
O(7A)—N(6A)—C(11A) | 118.47 (5) | N(5A)—C(9A)—C(10A) | 118.56 (4) |
C(2B)—N(1B)—C(4B) | 108.99 (4) | C(8A)—C(9A)—C(10A) | 121.23 (4) |
C(2B)—N(1B)—H(1B) | 126.29 (5) | C(9A)—C(10A)—C(11A) | 118.84 (4) |
C(4B)—N(1B)—H(1B) | 124.64 (4) | C(9A)—C(10A)—H(10A) | 120.40 (4) |
C(2B)—N(3B)—C(5B) | 109.11 (4) | C(11A)—C(10A)—H(10A) | 120.71 (4) |
C(2B)—N(3B)—H(3B) | 125.20 (5) | N(6A)—C(11A)—C(6A) | 119.06 (4) |
C(5B)—N(3B)—H(3B) | 125.68 (5) | N(6A)—C(11A)—C(10A) | 116.19 (3) |
O(2B)—N(4B)—O(3B) | 122.87 (6) | C(6A)—C(11A)—C(10A) | 124.74 (4) |
O(2B)—N(4B)—C(7B) | 119.20 (6) | N(1B)—C(2B)—N(3B) | 108.24 (5) |
O(3B)—N(4B)—C(7B) | 117.92 (5) | N(1B)—C(2B)—H(2B) | 124.81 (5) |
O(4B)—N(5B)—O(5B) | 122.93 (7) | N(3B)—C(2B)—H(2B) | 126.93 (4) |
O(4B)—N(5B)—C(9B) | 118.87 (5) | N(1B)—C(4B)—C(5B) | 107.13 (4) |
O(5B)—N(5B)—C(9B) | 118.19 (6) | N(1B)—C(4B)—H(4B) | 120.91 (4) |
O(6B)—N(6B)—O(7B) | 122.79 (7) | C(5B)—C(4B)—H(4B) | 131.91 (5) |
O(6B)—N(6B)—C(11B) | 117.82 (5) | N(3B)—C(5B)—C(4B) | 106.52 (4) |
O(7B)—N(6B)—C(11B) | 119.39 (6) | N(3B)—C(5B)—H(5B) | 121.79 (5) |
O(8)—C(12)—O(9) | 126.20 (6) | C(4B)—C(5B)—H(5B) | 131.69 (5) |
O(8)—C(12)—C(13) | 113.41 (5) | O(1B)—C(6B)—C(7B) | 125.16 (5) |
O(9)—C(12)—C(13) | 120.38 (5) | O(1B)—C(6B)—C(11B) | 123.17 (5) |
C(12)—C(13)—H(131) | 106.65 (3) | C(7B)—C(6B)—C(11B) | 111.66 (3) |
C(12)—C(13)—H(132) | 107.77 (3) | N(4B)—C(7B)—C(6B) | 119.74 (4) |
H(131)—C(13)—H(132) | 111.48 (4) | N(4B)—C(7B)—C(8B) | 115.62 (4) |
H(141)—C(14)—H(142) | 112.35 (4) | C(6B)—C(7B)—C(8B) | 124.59 (4) |
H(141)—C(14)—H(143) | 110.28 (5) | C(7B)—C(8B)—C(9B) | 118.91 (4) |
H(142)—C(14)—H(143) | 111.57 (4) | C(7B)—C(8B)—H(8B) | 120.06 (4) |
H(151)—C(15)—H(152) | 114.36 (6) | C(9B)—C(8B)—H(8B) | 121.03 (4) |
H(151)—C(15)—H(153) | 108.84 (5) | N(5B)—C(9B)—C(8B) | 119.94 (4) |
H(152)—C(15)—H(153) | 111.77 (5) | N(5B)—C(9B)—C(10B) | 118.95 (4) |
H(161)—C(16)—H(162) | 111.22 (6) | C(8B)—C(9B)—C(10B) | 121.11 (4) |
H(161)—C(16)—H(163) | 113.71 (7) | C(9B)—C(10B)—C(11B) | 119.66 (4) |
H(162)—C(16)—H(163) | 111.10 (6) | C(9B)—C(10B)—H(10B) | 119.79 (4) |
N(1A)—C(2A)—N(3A) | 108.74 (4) | C(11B)—C(10B)—H(10B) | 120.55 (4) |
N(1A)—C(2A)—H(2A) | 127.08 (5) | N(6B)—C(11B)—C(6B) | 120.19 (4) |
N(3A)—C(2A)—H(2A) | 124.14 (5) | N(6B)—C(11B)—C(10B) | 115.86 (4) |
N(3A)—C(4A)—C(5A) | 106.91 (4) | C(6B)—C(11B)—C(10B) | 123.90 (4) |
N(3A)—C(4A)—H(4A) | 121.92 (5) |
O(8)—C(12) | 1.2582 (7) | C(13)—H(131) | 1.0830 (4) |
O(9)—C(12) | 1.2461 (8) | C(13)—H(132) | 1.0830 (4) |
O(1A)—C(6A) | 1.2455 (7) | C(14)—H(141) | 1.0830 (5) |
O(2A)—N(4A) | 1.2329 (9) | C(14)—H(142) | 1.0830 (5) |
O(3A)—N(4A) | 1.2265 (9) | C(14)—H(143) | 1.0830 (5) |
O(4A)—N(5A) | 1.2283 (11) | C(15)—H(151) | 1.0830 (6) |
O(5A)—N(5A) | 1.2354 (9) | C(15)—H(152) | 1.0830 (7) |
O(6A)—N(6A) | 1.2353 (8) | C(15)—H(153) | 1.0830 (6) |
O(7A)—N(6A) | 1.2212 (9) | C(16)—H(161) | 1.0830 (8) |
O(1B)—C(6B) | 1.2429 (7) | C(16)—H(162) | 1.0830 (7) |
O(2B)—N(4B) | 1.2318 (8) | C(16)—H(163) | 1.0830 (6) |
O(3B)—N(4B) | 1.2251 (9) | C(2A)—H(2A) | 1.0830 (5) |
O(4B)—N(5B) | 1.2318 (11) | C(4A)—C(5A) | 1.3631 (7) |
O(5B)—N(5B) | 1.2392 (9) | C(4A)—H(4A) | 1.0830 (5) |
O(6B)—N(6B) | 1.2409 (8) | C(5A)—H(5A) | 1.0830 (6) |
O(7B)—N(6B) | 1.2246 (9) | C(6A)—C(7A) | 1.4529 (6) |
N(1A)—C(2A) | 1.3290 (7) | C(6A)—C(11A) | 1.4544 (5) |
N(1A)—C(5A) | 1.3743 (6) | C(7A)—C(8A) | 1.3864 (5) |
N(1A)—H(1A) | 1.0830 (4) | C(8A)—C(9A) | 1.3861 (5) |
N(3A)—C(2A) | 1.3330 (6) | C(8A)—H(8A) | 1.0830 (4) |
N(3A)—C(4A) | 1.3808 (7) | C(9A)—C(10A) | 1.3933 (6) |
N(3A)—H(3A) | 1.0830 (5) | C(10A)—C(11A) | 1.3706 (5) |
N(4A)—C(7A) | 1.4490 (5) | C(10A)—H(10A) | 1.0830 (4) |
N(5A)—C(9A) | 1.4460 (6) | C(2B)—H(2B) | 1.0830 (5) |
N(6A)—C(11A) | 1.4549 (6) | C(4B)—C(5B) | 1.3613 (6) |
N(1B)—C(2B) | 1.3293 (6) | C(4B)—H(4B) | 1.0830 (5) |
N(1B)—C(4B) | 1.3767 (7) | C(5B)—H(5B) | 1.0830 (5) |
N(1B)—H(1B) | 1.0830 (4) | C(6B)—C(7B) | 1.4601 (6) |
N(3B)—C(2B) | 1.3349 (6) | C(6B)—C(11B) | 1.4598 (5) |
N(3B)—C(5B) | 1.3784 (7) | C(7B)—C(8B) | 1.3785 (5) |
N(3B)—H(3B) | 1.0830 (4) | C(8B)—C(9B) | 1.3940 (6) |
N(4B)—C(7B) | 1.4553 (5) | C(8B)—H(8B) | 1.0830 (5) |
N(5B)—C(9B) | 1.4408 (6) | C(9B)—C(10B) | 1.3883 (6) |
N(6B)—C(11B) | 1.4537 (6) | C(10B)—C(11B) | 1.3796 (6) |
C(12)—C(13) | 1.5322 (5) | C(10B)—H(10B) | 1.0830 (4) |
C(2A)—N(1A)—C(5A) | 108.97 (4) | C(5A)—C(4A)—H(4A) | 131.15 (5) |
C(2A)—N(1A)—H(1A) | 122.03 (4) | N(1A)—C(5A)—C(4A) | 106.88 (5) |
C(5A)—N(1A)—H(1A) | 129.00 (5) | N(1A)—C(5A)—H(5A) | 122.06 (5) |
C(2A)—N(3A)—C(4A) | 108.50 (5) | C(4A)—C(5A)—H(5A) | 131.03 (5) |
C(2A)—N(3A)—H(3A) | 124.41 (5) | O(1A)—C(6A)—C(7A) | 126.20 (4) |
C(4A)—N(3A)—H(3A) | 126.86 (4) | O(1A)—C(6A)—C(11A) | 121.61 (5) |
O(2A)—N(4A)—O(3A) | 122.13 (6) | C(7A)—C(6A)—C(11A) | 112.14 (3) |
O(2A)—N(4A)—C(7A) | 119.52 (5) | N(4A)—C(7A)—C(6A) | 120.43 (4) |
O(3A)—N(4A)—C(7A) | 118.28 (5) | N(4A)—C(7A)—C(8A) | 116.00 (4) |
O(4A)—N(5A)—O(5A) | 123.94 (7) | C(6A)—C(7A)—C(8A) | 123.52 (3) |
O(4A)—N(5A)—C(9A) | 118.70 (6) | C(7A)—C(8A)—C(9A) | 119.52 (4) |
O(5A)—N(5A)—C(9A) | 117.36 (6) | C(7A)—C(8A)—H(8A) | 120.09 (4) |
O(6A)—N(6A)—O(7A) | 124.13 (7) | C(9A)—C(8A)—H(8A) | 120.37 (4) |
O(6A)—N(6A)—C(11A) | 117.38 (6) | N(5A)—C(9A)—C(8A) | 120.17 (4) |
O(7A)—N(6A)—C(11A) | 118.47 (5) | N(5A)—C(9A)—C(10A) | 118.56 (4) |
C(2B)—N(1B)—C(4B) | 108.99 (4) | C(8A)—C(9A)—C(10A) | 121.23 (4) |
C(2B)—N(1B)—H(1B) | 126.29 (5) | C(9A)—C(10A)—C(11A) | 118.84 (4) |
C(4B)—N(1B)—H(1B) | 124.64 (4) | C(9A)—C(10A)—H(10A) | 120.40 (4) |
C(2B)—N(3B)—C(5B) | 109.11 (4) | C(11A)—C(10A)—H(10A) | 120.71 (4) |
C(2B)—N(3B)—H(3B) | 125.20 (5) | N(6A)—C(11A)—C(6A) | 119.06 (4) |
C(5B)—N(3B)—H(3B) | 125.68 (5) | N(6A)—C(11A)—C(10A) | 116.19 (3) |
O(2B)—N(4B)—O(3B) | 122.87 (6) | C(6A)—C(11A)—C(10A) | 124.74 (4) |
O(2B)—N(4B)—C(7B) | 119.20 (6) | N(1B)—C(2B)—N(3B) | 108.24 (5) |
O(3B)—N(4B)—C(7B) | 117.92 (5) | N(1B)—C(2B)—H(2B) | 124.81 (5) |
O(4B)—N(5B)—O(5B) | 122.93 (7) | N(3B)—C(2B)—H(2B) | 126.93 (4) |
O(4B)—N(5B)—C(9B) | 118.87 (5) | N(1B)—C(4B)—C(5B) | 107.13 (4) |
O(5B)—N(5B)—C(9B) | 118.19 (6) | N(1B)—C(4B)—H(4B) | 120.91 (4) |
O(6B)—N(6B)—O(7B) | 122.79 (7) | C(5B)—C(4B)—H(4B) | 131.91 (5) |
O(6B)—N(6B)—C(11B) | 117.82 (5) | N(3B)—C(5B)—C(4B) | 106.52 (4) |
O(7B)—N(6B)—C(11B) | 119.39 (6) | N(3B)—C(5B)—H(5B) | 121.79 (5) |
O(8)—C(12)—O(9) | 126.20 (6) | C(4B)—C(5B)—H(5B) | 131.69 (5) |
O(8)—C(12)—C(13) | 113.41 (5) | O(1B)—C(6B)—C(7B) | 125.16 (5) |
O(9)—C(12)—C(13) | 120.38 (5) | O(1B)—C(6B)—C(11B) | 123.17 (5) |
C(12)—C(13)—H(131) | 106.65 (3) | C(7B)—C(6B)—C(11B) | 111.66 (3) |
C(12)—C(13)—H(132) | 107.77 (3) | N(4B)—C(7B)—C(6B) | 119.74 (4) |
H(131)—C(13)—H(132) | 111.48 (4) | N(4B)—C(7B)—C(8B) | 115.62 (4) |
H(141)—C(14)—H(142) | 112.35 (4) | C(6B)—C(7B)—C(8B) | 124.59 (4) |
H(141)—C(14)—H(143) | 110.28 (5) | C(7B)—C(8B)—C(9B) | 118.91 (4) |
H(142)—C(14)—H(143) | 111.57 (4) | C(7B)—C(8B)—H(8B) | 120.06 (4) |
H(151)—C(15)—H(152) | 114.36 (6) | C(9B)—C(8B)—H(8B) | 121.03 (4) |
H(151)—C(15)—H(153) | 108.84 (5) | N(5B)—C(9B)—C(8B) | 119.94 (4) |
H(152)—C(15)—H(153) | 111.77 (5) | N(5B)—C(9B)—C(10B) | 118.95 (4) |
H(161)—C(16)—H(162) | 111.22 (6) | C(8B)—C(9B)—C(10B) | 121.11 (4) |
H(161)—C(16)—H(163) | 113.71 (7) | C(9B)—C(10B)—C(11B) | 119.66 (4) |
H(162)—C(16)—H(163) | 111.10 (6) | C(9B)—C(10B)—H(10B) | 119.79 (4) |
N(1A)—C(2A)—N(3A) | 108.74 (4) | C(11B)—C(10B)—H(10B) | 120.55 (4) |
N(1A)—C(2A)—H(2A) | 127.08 (5) | N(6B)—C(11B)—C(6B) | 120.19 (4) |
N(3A)—C(2A)—H(2A) | 124.14 (5) | N(6B)—C(11B)—C(10B) | 115.86 (4) |
N(3A)—C(4A)—C(5A) | 106.91 (4) | C(6B)—C(11B)—C(10B) | 123.90 (4) |
N(3A)—C(4A)—H(4A) | 121.92 (5) |
O(8)—C(12) | 1.2599 (8) | C(13)—H(131) | 1.0830 (6) |
O(9)—C(12) | 1.2484 (8) | C(13)—H(132) | 1.0830 (6) |
O(1A)—C(6A) | 1.2452 (7) | C(14)—H(141) | 1.0830 (7) |
O(2A)—N(4A) | 1.2367 (8) | C(14)—H(142) | 1.0830 (7) |
O(3A)—N(4A) | 1.2300 (8) | C(14)—H(143) | 1.0830 (7) |
O(4A)—N(5A) | 1.2302 (9) | C(15)—H(151) | 1.0830 (7) |
O(5A)—N(5A) | 1.2355 (8) | C(15)—H(152) | 1.0830 (9) |
O(6A)—N(6A) | 1.2372 (7) | C(15)—H(153) | 1.0830 (7) |
O(7A)—N(6A) | 1.2208 (8) | C(16)—H(161) | 1.0830 (10) |
O(1B)—C(6B) | 1.2427 (8) | C(16)—H(162) | 1.0830 (9) |
O(2B)—N(4B) | 1.2362 (7) | C(16)—H(163) | 1.0830 (8) |
O(3B)—N(4B) | 1.2241 (8) | C(2A)—H(2A) | 1.0830 (7) |
O(4B)—N(5B) | 1.2339 (9) | C(4A)—C(5A) | 1.3584 (10) |
O(5B)—N(5B) | 1.2402 (8) | C(4A)—H(4A) | 1.0830 (6) |
O(6B)—N(6B) | 1.2424 (7) | C(5A)—H(5A) | 1.0830 (7) |
O(7B)—N(6B) | 1.2233 (8) | C(6A)—C(7A) | 1.4510 (8) |
N(1A)—C(2A) | 1.3254 (9) | C(6A)—C(11A) | 1.4550 (7) |
N(1A)—C(5A) | 1.3755 (8) | C(7A)—C(8A) | 1.3868 (8) |
N(1A)—H(1A) | 1.0830 (5) | C(8A)—C(9A) | 1.3867 (8) |
N(3A)—C(2A) | 1.3348 (8) | C(8A)—H(8A) | 1.0830 (6) |
N(3A)—C(4A) | 1.3782 (10) | C(9A)—C(10A) | 1.3904 (9) |
N(3A)—H(3A) | 1.0830 (6) | C(10A)—C(11A) | 1.3724 (8) |
N(4A)—C(7A) | 1.4514 (7) | C(10A)—H(10A) | 1.0830 (5) |
N(5A)—C(9A) | 1.4479 (8) | C(2B)—H(2B) | 1.0830 (7) |
N(6A)—C(11A) | 1.4567 (8) | C(4B)—C(5B) | 1.3593 (9) |
N(1B)—C(2B) | 1.3320 (8) | C(4B)—H(4B) | 1.0830 (6) |
N(1B)—C(4B) | 1.3729 (9) | C(5B)—H(5B) | 1.0830 (7) |
N(1B)—H(1B) | 1.0830 (5) | C(6B)—C(7B) | 1.4601 (8) |
N(3B)—C(2B) | 1.3348 (9) | C(6B)—C(11B) | 1.4600 (8) |
N(3B)—C(5B) | 1.3777 (10) | C(7B)—C(8B) | 1.3768 (8) |
N(3B)—H(3B) | 1.0830 (5) | C(8B)—C(9B) | 1.3929 (8) |
N(4B)—C(7B) | 1.4573 (7) | C(8B)—H(8B) | 1.0830 (6) |
N(5B)—C(9B) | 1.4453 (8) | C(9B)—C(10B) | 1.3837 (9) |
N(6B)—C(11B) | 1.4557 (8) | C(10B)—C(11B) | 1.3808 (8) |
C(12)—C(13) | 1.5340 (8) | C(10B)—H(10B) | 1.0830 (6) |
C(2A)—N(1A)—C(5A) | 109.01 (5) | C(5A)—C(4A)—H(4A) | 131.17 (7) |
C(2A)—N(1A)—H(1A) | 122.03 (5) | N(1A)—C(5A)—C(4A) | 106.88 (6) |
C(5A)—N(1A)—H(1A) | 128.96 (6) | N(1A)—C(5A)—H(5A) | 121.92 (6) |
C(2A)—N(3A)—C(4A) | 108.50 (6) | C(4A)—C(5A)—H(5A) | 131.17 (6) |
C(2A)—N(3A)—H(3A) | 124.28 (6) | O(1A)—C(6A)—C(7A) | 126.32 (5) |
C(4A)—N(3A)—H(3A) | 126.98 (6) | O(1A)—C(6A)—C(11A) | 121.67 (5) |
O(2A)—N(4A)—O(3A) | 122.23 (5) | C(7A)—C(6A)—C(11A) | 111.96 (5) |
O(2A)—N(4A)—C(7A) | 119.42 (5) | N(4A)—C(7A)—C(6A) | 120.30 (5) |
O(3A)—N(4A)—C(7A) | 118.30 (5) | N(4A)—C(7A)—C(8A) | 115.80 (5) |
O(4A)—N(5A)—O(5A) | 123.74 (6) | C(6A)—C(7A)—C(8A) | 123.86 (5) |
O(4A)—N(5A)—C(9A) | 118.70 (6) | C(7A)—C(8A)—C(9A) | 119.10 (5) |
O(5A)—N(5A)—C(9A) | 117.55 (6) | C(7A)—C(8A)—H(8A) | 120.34 (5) |
O(6A)—N(6A)—O(7A) | 124.17 (6) | C(9A)—C(8A)—H(8A) | 120.54 (5) |
O(6A)—N(6A)—C(11A) | 117.26 (5) | N(5A)—C(9A)—C(8A) | 120.02 (6) |
O(7A)—N(6A)—C(11A) | 118.56 (5) | N(5A)—C(9A)—C(10A) | 118.35 (5) |
C(2B)—N(1B)—C(4B) | 109.11 (5) | C(8A)—C(9A)—C(10A) | 121.60 (5) |
C(2B)—N(1B)—H(1B) | 125.95 (6) | C(9A)—C(10A)—C(11A) | 118.65 (5) |
C(4B)—N(1B)—H(1B) | 124.88 (5) | C(9A)—C(10A)—H(10A) | 120.67 (5) |
C(2B)—N(3B)—C(5B) | 109.19 (5) | C(11A)—C(10A)—H(10A) | 120.63 (6) |
C(2B)—N(3B)—H(3B) | 125.18 (6) | N(6A)—C(11A)—C(6A) | 118.98 (5) |
C(5B)—N(3B)—H(3B) | 125.62 (6) | N(6A)—C(11A)—C(10A) | 116.21 (5) |
O(2B)—N(4B)—O(3B) | 122.98 (6) | C(6A)—C(11A)—C(10A) | 124.81 (5) |
O(2B)—N(4B)—C(7B) | 118.97 (5) | N(1B)—C(2B)—N(3B) | 107.98 (6) |
O(3B)—N(4B)—C(7B) | 118.04 (5) | N(1B)—C(2B)—H(2B) | 125.02 (6) |
O(4B)—N(5B)—O(5B) | 123.15 (6) | N(3B)—C(2B)—H(2B) | 126.99 (6) |
O(4B)—N(5B)—C(9B) | 118.84 (5) | N(1B)—C(4B)—C(5B) | 107.19 (6) |
O(5B)—N(5B)—C(9B) | 118.01 (6) | N(1B)—C(4B)—H(4B) | 120.85 (6) |
O(6B)—N(6B)—O(7B) | 122.68 (6) | C(5B)—C(4B)—H(4B) | 131.92 (7) |
O(6B)—N(6B)—C(11B) | 117.87 (5) | N(3B)—C(5B)—C(4B) | 106.53 (6) |
O(7B)—N(6B)—C(11B) | 119.44 (5) | N(3B)—C(5B)—H(5B) | 121.78 (6) |
O(8)—C(12)—O(9) | 126.43 (6) | C(4B)—C(5B)—H(5B) | 131.68 (7) |
O(8)—C(12)—C(13) | 113.15 (5) | O(1B)—C(6B)—C(7B) | 125.29 (5) |
O(9)—C(12)—C(13) | 120.41 (5) | O(1B)—C(6B)—C(11B) | 123.31 (6) |
C(12)—C(13)—H(131) | 106.73 (5) | C(7B)—C(6B)—C(11B) | 111.40 (5) |
C(12)—C(13)—H(132) | 107.72 (5) | N(4B)—C(7B)—C(6B) | 119.64 (5) |
H(131)—C(13)—H(132) | 111.70 (5) | N(4B)—C(7B)—C(8B) | 115.47 (5) |
H(141)—C(14)—H(142) | 112.49 (6) | C(6B)—C(7B)—C(8B) | 124.84 (5) |
H(141)—C(14)—H(143) | 110.67 (6) | C(7B)—C(8B)—C(9B) | 118.62 (6) |
H(142)—C(14)—H(143) | 111.58 (6) | C(7B)—C(8B)—H(8B) | 120.20 (5) |
H(151)—C(15)—H(152) | 114.18 (8) | C(9B)—C(8B)—H(8B) | 121.18 (5) |
H(151)—C(15)—H(153) | 108.92 (7) | N(5B)—C(9B)—C(8B) | 119.70 (6) |
H(152)—C(15)—H(153) | 111.89 (7) | N(5B)—C(9B)—C(10B) | 118.78 (5) |
H(161)—C(16)—H(162) | 111.46 (7) | C(8B)—C(9B)—C(10B) | 121.51 (5) |
H(161)—C(16)—H(163) | 114.51 (8) | C(9B)—C(10B)—C(11B) | 119.40 (5) |
H(162)—C(16)—H(163) | 110.87 (7) | C(9B)—C(10B)—H(10B) | 120.15 (5) |
N(1A)—C(2A)—N(3A) | 108.62 (6) | C(11B)—C(10B)—H(10B) | 120.45 (6) |
N(1A)—C(2A)—H(2A) | 127.28 (6) | N(6B)—C(11B)—C(6B) | 120.00 (5) |
N(3A)—C(2A)—H(2A) | 124.07 (6) | N(6B)—C(11B)—C(10B) | 115.89 (5) |
N(3A)—C(4A)—C(5A) | 106.99 (6) | C(6B)—C(11B)—C(10B) | 124.07 (6) |
N(3A)—C(4A)—H(4A) | 121.82 (6) |
O(8)—C(12) | 1.2575 (10) | C(13)—H(131) | 1.0830 (8) |
O(9)—C(12) | 1.2477 (12) | C(13)—H(132) | 1.0830 (7) |
O(1A)—C(6A) | 1.2461 (10) | C(14)—H(141) | 1.0830 (9) |
O(2A)—N(4A) | 1.2339 (12) | C(14)—H(142) | 1.0830 (11) |
O(3A)—N(4A) | 1.2271 (13) | C(14)—H(143) | 1.0830 (11) |
O(4A)—N(5A) | 1.2292 (17) | C(15)—H(151) | 1.0830 (11) |
O(5A)—N(5A) | 1.2355 (13) | C(15)—H(152) | 1.0830 (17) |
O(6A)—N(6A) | 1.2360 (11) | C(15)—H(153) | 1.0830 (11) |
O(7A)—N(6A) | 1.2206 (14) | C(16)—H(161) | 1.083 (2) |
O(1B)—C(6B) | 1.2427 (10) | C(16)—H(162) | 1.0830 (18) |
O(2B)—N(4B) | 1.2331 (12) | C(16)—H(163) | 1.0830 (13) |
O(3B)—N(4B) | 1.2236 (13) | C(2A)—H(2A) | 1.0830 (9) |
O(4B)—N(5B) | 1.2318 (16) | C(4A)—C(5A) | 1.3636 (15) |
O(5B)—N(5B) | 1.2399 (13) | C(4A)—H(4A) | 1.0830 (8) |
O(6B)—N(6B) | 1.2406 (11) | C(5A)—H(5A) | 1.0830 (11) |
O(7B)—N(6B) | 1.2225 (13) | C(6A)—C(7A) | 1.4522 (11) |
N(1A)—C(2A) | 1.3276 (14) | C(6A)—C(11A) | 1.4564 (8) |
N(1A)—C(5A) | 1.3750 (11) | C(7A)—C(8A) | 1.3857 (10) |
N(1A)—H(1A) | 1.0830 (6) | C(8A)—C(9A) | 1.3875 (9) |
N(3A)—C(2A) | 1.3329 (12) | C(8A)—H(8A) | 1.0830 (8) |
N(3A)—C(4A) | 1.3828 (15) | C(9A)—C(10A) | 1.3949 (12) |
N(3A)—H(3A) | 1.0830 (9) | C(10A)—C(11A) | 1.3687 (10) |
N(4A)—C(7A) | 1.4501 (8) | C(10A)—H(10A) | 1.0830 (6) |
N(5A)—C(9A) | 1.4458 (9) | C(2B)—H(2B) | 1.0830 (10) |
N(6A)—C(11A) | 1.4548 (11) | C(4B)—C(5B) | 1.3605 (13) |
N(1B)—C(2B) | 1.3288 (11) | C(4B)—H(4B) | 1.0830 (9) |
N(1B)—C(4B) | 1.3761 (14) | C(5B)—H(5B) | 1.0830 (10) |
N(1B)—H(1B) | 1.0830 (6) | C(6B)—C(7B) | 1.4620 (11) |
N(3B)—C(2B) | 1.3342 (12) | C(6B)—C(11B) | 1.4595 (9) |
N(3B)—C(5B) | 1.3770 (16) | C(7B)—C(8B) | 1.3760 (10) |
N(3B)—H(3B) | 1.0830 (7) | C(8B)—C(9B) | 1.3935 (10) |
N(4B)—C(7B) | 1.4576 (9) | C(8B)—H(8B) | 1.0830 (8) |
N(5B)—C(9B) | 1.4411 (10) | C(9B)—C(10B) | 1.3879 (12) |
N(6B)—C(11B) | 1.4536 (11) | C(10B)—C(11B) | 1.3797 (10) |
C(12)—C(13) | 1.5337 (10) | C(10B)—H(10B) | 1.0830 (7) |
C(2A)—N(1A)—C(5A) | 109.04 (7) | C(5A)—C(4A)—H(4A) | 131.39 (11) |
C(2A)—N(1A)—H(1A) | 122.13 (7) | N(1A)—C(5A)—C(4A) | 106.83 (9) |
C(5A)—N(1A)—H(1A) | 128.83 (9) | N(1A)—C(5A)—H(5A) | 122.22 (9) |
C(2A)—N(3A)—C(4A) | 108.44 (9) | C(4A)—C(5A)—H(5A) | 130.91 (8) |
C(2A)—N(3A)—H(3A) | 124.33 (9) | O(1A)—C(6A)—C(7A) | 126.40 (6) |
C(4A)—N(3A)—H(3A) | 127.01 (8) | O(1A)—C(6A)—C(11A) | 121.52 (7) |
O(2A)—N(4A)—O(3A) | 122.24 (7) | C(7A)—C(6A)—C(11A) | 112.05 (6) |
O(2A)—N(4A)—C(7A) | 119.49 (8) | N(4A)—C(7A)—C(6A) | 120.30 (6) |
O(3A)—N(4A)—C(7A) | 118.21 (7) | N(4A)—C(7A)—C(8A) | 115.97 (7) |
O(4A)—N(5A)—O(5A) | 123.94 (9) | C(6A)—C(7A)—C(8A) | 123.68 (6) |
O(4A)—N(5A)—C(9A) | 118.73 (8) | C(7A)—C(8A)—C(9A) | 119.39 (7) |
O(5A)—N(5A)—C(9A) | 117.32 (9) | C(7A)—C(8A)—H(8A) | 120.19 (6) |
O(6A)—N(6A)—O(7A) | 124.15 (10) | C(9A)—C(8A)—H(8A) | 120.40 (7) |
O(6A)—N(6A)—C(11A) | 117.29 (9) | N(5A)—C(9A)—C(8A) | 120.10 (7) |
O(7A)—N(6A)—C(11A) | 118.55 (7) | N(5A)—C(9A)—C(10A) | 118.60 (7) |
C(2B)—N(1B)—C(4B) | 108.90 (7) | C(8A)—C(9A)—C(10A) | 121.26 (6) |
C(2B)—N(1B)—H(1B) | 126.29 (8) | C(9A)—C(10A)—C(11A) | 118.80 (6) |
C(4B)—N(1B)—H(1B) | 124.75 (7) | C(9A)—C(10A)—H(10A) | 120.29 (7) |
C(2B)—N(3B)—C(5B) | 109.16 (7) | C(11A)—C(10A)—H(10A) | 120.86 (8) |
C(2B)—N(3B)—H(3B) | 125.10 (9) | N(6A)—C(11A)—C(6A) | 119.05 (6) |
C(5B)—N(3B)—H(3B) | 125.73 (9) | N(6A)—C(11A)—C(10A) | 116.15 (6) |
O(2B)—N(4B)—O(3B) | 122.97 (8) | C(6A)—C(11A)—C(10A) | 124.80 (7) |
O(2B)—N(4B)—C(7B) | 119.16 (8) | N(1B)—C(2B)—N(3B) | 108.26 (8) |
O(3B)—N(4B)—C(7B) | 117.87 (7) | N(1B)—C(2B)—H(2B) | 124.75 (8) |
O(4B)—N(5B)—O(5B) | 123.12 (9) | N(3B)—C(2B)—H(2B) | 126.97 (8) |
O(4B)—N(5B)—C(9B) | 118.81 (8) | N(1B)—C(4B)—C(5B) | 107.22 (8) |
O(5B)—N(5B)—C(9B) | 118.06 (10) | N(1B)—C(4B)—H(4B) | 120.80 (8) |
O(6B)—N(6B)—O(7B) | 122.88 (10) | C(5B)—C(4B)—H(4B) | 131.94 (11) |
O(6B)—N(6B)—C(11B) | 117.69 (8) | N(3B)—C(5B)—C(4B) | 106.46 (9) |
O(7B)—N(6B)—C(11B) | 119.41 (8) | N(3B)—C(5B)—H(5B) | 121.82 (9) |
O(8)—C(12)—O(9) | 126.25 (7) | C(4B)—C(5B)—H(5B) | 131.71 (11) |
O(8)—C(12)—C(13) | 113.39 (7) | O(1B)—C(6B)—C(7B) | 125.17 (7) |
O(9)—C(12)—C(13) | 120.34 (7) | O(1B)—C(6B)—C(11B) | 123.24 (8) |
C(12)—C(13)—H(131) | 106.59 (6) | C(7B)—C(6B)—C(11B) | 111.59 (6) |
C(12)—C(13)—H(132) | 107.67 (5) | N(4B)—C(7B)—C(6B) | 119.65 (6) |
H(131)—C(13)—H(132) | 111.63 (7) | N(4B)—C(7B)—C(8B) | 115.63 (7) |
H(141)—C(14)—H(142) | 112.44 (8) | C(6B)—C(7B)—C(8B) | 124.67 (6) |
H(141)—C(14)—H(143) | 110.22 (9) | C(7B)—C(8B)—C(9B) | 118.92 (8) |
H(142)—C(14)—H(143) | 111.74 (9) | C(7B)—C(8B)—H(8B) | 120.05 (7) |
H(151)—C(15)—H(152) | 114.56 (14) | C(9B)—C(8B)—H(8B) | 121.03 (7) |
H(151)—C(15)—H(153) | 108.70 (10) | N(5B)—C(9B)—C(8B) | 119.94 (8) |
H(152)—C(15)—H(153) | 112.02 (10) | N(5B)—C(9B)—C(10B) | 118.98 (7) |
H(161)—C(16)—H(162) | 111.45 (12) | C(8B)—C(9B)—C(10B) | 121.08 (7) |
H(161)—C(16)—H(163) | 113.16 (17) | C(9B)—C(10B)—C(11B) | 119.73 (6) |
H(162)—C(16)—H(163) | 111.22 (13) | C(9B)—C(10B)—H(10B) | 119.74 (7) |
N(1A)—C(2A)—N(3A) | 108.81 (8) | C(11B)—C(10B)—H(10B) | 120.51 (8) |
N(1A)—C(2A)—H(2A) | 126.99 (8) | N(6B)—C(11B)—C(6B) | 120.17 (6) |
N(3A)—C(2A)—H(2A) | 124.17 (10) | N(6B)—C(11B)—C(10B) | 115.94 (6) |
N(3A)—C(4A)—C(5A) | 106.88 (7) | C(6B)—C(11B)—C(10B) | 123.85 (7) |
N(3A)—C(4A)—H(4A) | 121.72 (10) |