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Accurate atomic displacement parameters (ADPs) are a good indication of high-quality diffraction data. Results from the newly commissioned time-of-flight Laue diffractometer TOPAZ at the SNS are presented. Excellent agreement is found between ADPs derived independently from the neutron and X-ray data emphasizing the high quality of the data from the time-of-flight Laue diffractometer.
Supporting information
![cif](https://journals.iucr.org//../logos/filetypeicons/bw/b1/ciflogo.png) | Crystallographic Information File (CIF) https://doi.org/10.1107/S2053273314015599/pc5039sup1.cif Contains datablocks global, Rubrene_neutron, Rubrene_Xray_multipolemodel, Rubrene_Xray_MM_Shade, Rubrene_Xray_IAM, Rubrene_Xray_IAM_HO, Rubrene_HAR, BIPa_neutron_100K, BIPa_X_multipole_model, BIPa_X_MM_Shade, BIPa_Xray_IAM, BIPa_X_HO_IAM |
![pdf](https://journals.iucr.org//../logos/filetypeicons/bw/b1/pdflogo.png) | Portable Document Format (PDF) file https://doi.org/10.1107/S2053273314015599/pc5039sup2.pdf Supporting information |
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.
(Rubrene_neutron) 5,6,11,12-tetraphenyltetracene
top
Crystal data top
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 | |
Data collection top
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 top
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 | |
Crystal data top
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 |
Data collection top
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) |
Refinement top
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 | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
(Rubrene_Xray_multipolemodel) 5,6,11,12-tetraphenyltetracene
top
Crystal data top
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 |
Data collection top
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 top
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 |
Crystal data top
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 |
Data collection top
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 | |
Refinement top
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 |
Special details top
Experimental. A nitrogen gas-flow low temperature device was used for cooling. A face indexed analytical absorption correction was performed. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
(Rubrene_Xray_MM_Shade)
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Crystal data top
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 |
Data collection top
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 | |
Refinement top
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 | |
Special details top
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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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 |
Geometric parameters (Å, º) top
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. |
(Rubrene_Xray_IAM) 5,6,11,12-tetraphenyltetracene
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Crystal data top
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 |
Data collection top
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 | |
Refinement top
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 | |
Special details top
Experimental. A nitrogen gas-flow low temperature device was used for cooling. A face indexed analytical absorption correction was performed. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
(Rubrene_Xray_IAM_HO) 5,6,11,12-tetraphenyltetracene
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Crystal data top
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 |
Data collection top
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 | |
Refinement top
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 | |
Special details top
Experimental. A nitrogen gas-flow low temperature device was used for cooling. A face indexed analytical absorption correction was performed. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
(Rubrene_HAR) 5,6,11,12-tetraphenyltetracene
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Crystal data top
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 |
Data collection top
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 | |
Refinement top
wR(F2) = 0.033 | 159 parameters |
S = 2.96 | 0 restraints |
6289 reflections | All H-atom parameters refined |
Special details top
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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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) |
(BIPa_neutron_100K) cocrystal between picric acid, imidazole and betaine
top
Crystal data top
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) |
Data collection top
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 top
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 | |
Crystal data top
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)° | |
Data collection top
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) |
Refinement top
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 | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
(BIPa_X_multipole_model) cocrystal between picric acid, imidazole and betaine
top
Crystal data top
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 | |
Data collection top
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 top
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 |
Crystal data top
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)° | |
Data collection top
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 | |
Refinement top
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 |
Special details top
Refinement. Charge density modeled in XD2006 using the Hansen-Coppens multipole model. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
(BIPa_X_MM_Shade) cocrystal between picric acid, imidazole and betaine
top
Crystal data top
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 | |
Data collection top
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 top
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 | |
Crystal data top
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)° | |
Data collection top
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 | |
Refinement top
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 | |
Special details top
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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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 |
Geometric parameters (Å, º) top
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) | | |
(BIPa_Xray_IAM) cocrystal between picric acid, imidazole and betaine
top
Crystal data top
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 | |
Data collection top
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 top
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 |
Crystal data top
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)° | |
Data collection top
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 | |
Refinement top
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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
(BIPa_X_HO_IAM) cocrystal between picric acid, imidazole and betaine
top
Crystal data top
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 | |
Data collection top
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 top
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 |
Crystal data top
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)° | |
Data collection top
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 | |
Refinement top
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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
Selected geometric parameters (Å, º) for (Rubrene_Xray_multipolemodel) topC(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. |
Selected geometric parameters (Å, º) for (Rubrene_Xray_MM_Shade) topC(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. |
Selected geometric parameters (Å, º) for (Rubrene_Xray_IAM) topC(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. |
Selected geometric parameters (Å, º) for (Rubrene_Xray_IAM_HO) topC(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. |
Selected geometric parameters (Å, º) for (BIPa_X_multipole_model) topO(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) | | |
Selected geometric parameters (Å, º) for (BIPa_X_MM_Shade) topO(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) | | |
Selected geometric parameters (Å, º) for (BIPa_Xray_IAM) topO(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) | | |
Selected geometric parameters (Å, º) for (BIPa_X_HO_IAM) topO(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) | | |
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