Download citation
Download citation
link to html
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

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

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

Computing details top

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
C42H28F(000) = 697.76
Mr = 532.69Dx = 1.299 Mg m3
Orthorhombic, CmcaNeutron radiation, λ = 0.4-3.4 Å
Hall symbol: -C 2bc 2Cell parameters from 1000 reflections
a = 26.7972 (3) ŵ = 0.20 mm1
b = 7.1617 (1) ÅT = 100 K
c = 14.1940 (2) ÅBlock, red
V = 2724.01 (5) Å31.50 × 1.50 × 1.00 mm
Z = 4
Data collection top
TOPAZ Single Crystal Diffractometer24945 measured reflections
Radiation source: spallation neutron source, SNS BL1222955 independent reflections
Not applicable to TOF Laue technique monochromator22955 reflections with > 3σ(I)
time–of–flight Laue scansh = 5863
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 = 179
Tmin = 0.646, Tmax = 0.848l = 3434
Refinement top
Refinement on F2All H-atom parameters refined
Least-squares matrix: fullWeighting scheme based on measured s.u.'s
R[F2 > 2σ(F2)] = 0.046(Δ/σ)max < 0.001
wR(F2) = 0.055Δρmax = 0.23 e Å3
S = 1.57Δρmin = 0.31 e Å3
22775 reflectionsExtinction correction: B-C Secondary type 1 Lorenzian
182 parametersExtinction coefficient: 0.08E-05 (3)
0 restraints
Crystal data top
C42H28V = 2724.01 (5) Å3
Mr = 532.69Z = 4
Orthorhombic, CmcaNeutron radiation, λ = 0.4-3.4 Å
a = 26.7972 (3) ŵ = 0.20 mm1
b = 7.1617 (1) ÅT = 100 K
c = 14.1940 (2) Å1.50 × 1.50 × 1.00 mm
Data collection top
TOPAZ Single Crystal Diffractometer24945 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 = 0.84822955 reflections with > 3σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.055All H-atom parameters refined
S = 1.57Δρmax = 0.23 e Å3
22775 reflectionsΔρmin = 0.31 e Å3
182 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.027308 (14)0.00.00.00978
C20.053187 (10)0.14434 (4)0.048949 (17)0.01041
C30.026811 (10)0.29586 (4)0.087630 (17)0.01059
C40.052041 (11)0.44708 (4)0.133976 (19)0.01351
C50.026484 (12)0.58998 (4)0.17539 (2)0.0152
C60.107508 (10)0.13462 (4)0.072664 (17)0.01121
C70.142796 (11)0.24848 (5)0.02859 (2)0.01465
C80.192043 (12)0.25130 (5)0.05955 (2)0.01876
C90.207040 (12)0.13900 (5)0.13453 (2)0.0211
C100.172212 (13)0.02479 (5)0.17886 (2)0.0203
C110.122818 (12)0.02353 (5)0.148310 (19)0.01548
H40.09247 (3)0.44660 (12)0.13632 (5)0.0307
H50.04640 (3)0.70248 (12)0.21052 (6)0.03414
H70.13131 (3)0.33549 (12)0.03021 (5)0.03286
H80.21886 (3)0.34232 (14)0.02525 (7)0.03953
H90.24554 (3)0.14180 (15)0.15836 (6)0.04295
H100.18338 (3)0.06333 (15)0.23747 (6)0.04324
H110.09552 (3)0.06350 (13)0.18360 (5)0.03518
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.00972 (14)0.00961 (16)0.01000 (12)0.00.00.00128 (10)
C20.01055 (10)0.00988 (11)0.01081 (9)0.00085 (8)0.00014 (7)0.00104 (7)
C30.01197 (10)0.00962 (11)0.01017 (9)0.00081 (8)0.00030 (7)0.00145 (7)
C40.01527 (12)0.01163 (12)0.01362 (10)0.00258 (9)0.00125 (8)0.00323 (8)
C50.01890 (13)0.01151 (13)0.01519 (11)0.00195 (10)0.00095 (9)0.00431 (9)
C60.01057 (10)0.01180 (12)0.01127 (9)0.00134 (8)0.00027 (7)0.00068 (8)
C70.01196 (11)0.01435 (14)0.01764 (11)0.00161 (9)0.00217 (9)0.00129 (9)
C80.01101 (12)0.02017 (16)0.02509 (14)0.00269 (10)0.00259 (10)0.00194 (11)
C90.01212 (13)0.02789 (19)0.02328 (13)0.00009 (11)0.00322 (10)0.00430 (12)
C100.01691 (14)0.02736 (19)0.01664 (11)0.00163 (12)0.00526 (10)0.00124 (11)
C110.01433 (13)0.01907 (15)0.01303 (10)0.00120 (10)0.00179 (9)0.00265 (9)
H40.0205 (3)0.0317 (4)0.0400 (3)0.0049 (3)0.0018 (3)0.0113 (3)
H50.0346 (4)0.0264 (4)0.0415 (4)0.0077 (3)0.0003 (3)0.0152 (3)
H70.0301 (4)0.0336 (4)0.0349 (3)0.0016 (3)0.0010 (3)0.0146 (3)
H80.0239 (4)0.0387 (5)0.0560 (5)0.0087 (3)0.0080 (3)0.0074 (4)
H90.0201 (4)0.0592 (6)0.0495 (5)0.0011 (3)0.0097 (3)0.0017 (4)
H100.0379 (5)0.0575 (6)0.0343 (4)0.0046 (4)0.0126 (3)0.0157 (4)
H110.0297 (4)0.0417 (5)0.0342 (3)0.0082 (3)0.0004 (3)0.0156 (3)
Geometric parameters (Å, º) top
C1—C1i1.4636 (8)C6—C111.3980 (4)
C1—C21.4256 (3)C7—C81.3911 (4)
C2—C31.4067 (4)C7—H71.0862 (8)
C2—C61.4957 (4)C8—C91.3931 (5)
C3—C3i1.4370 (5)C8—H81.0855 (9)
C3—C41.4362 (4)C9—C101.3914 (5)
C4—C51.3646 (4)C9—H91.0858 (9)
C4—H41.0839 (8)C10—C111.3929 (5)
C5—C5i1.4194 (6)C10—H101.0863 (9)
C5—H51.0875 (8)C11—C61.3980 (4)
C6—C71.3966 (4)C11—H111.0837 (8)
C1i—C1—C2119.109 (17)C7—C6—C11118.53 (3)
C2—C1—C2ii121.78 (3)C6—C7—C8120.62 (3)
C1—C2—C3120.34 (3)C6—C7—H7119.16 (5)
C1—C2—C6123.33 (3)C8—C7—H7120.22 (5)
C3—C2—C6115.92 (2)C7—C8—C9120.44 (3)
C2—C3—C3i120.164 (15)C7—C8—H8119.67 (6)
C2—C3—C4121.60 (3)C9—C8—H8119.89 (6)
C3i—C3—C4118.084 (16)C8—C9—C10119.43 (3)
C3—C4—C5121.78 (3)C8—C9—H9120.09 (6)
C3—C4—H4118.83 (5)C10—C9—H9120.48 (6)
C5—C4—H4119.39 (5)C9—C10—C11120.03 (3)
C4—C5—C5i120.126 (18)C9—C10—H10120.21 (6)
C4—C5—H5120.46 (5)C11—C10—H10119.76 (6)
C5i—C5—H5119.39 (5)C6—C11—C10120.95 (3)
C2—C6—C7122.08 (3)C6—C11—H11118.97 (5)
C2—C6—C11119.01 (2)C10—C11—H11120.08 (5)
Symmetry codes: (i) x, y, z; (ii) x, y, z.
(Rubrene_Xray_multipolemodel) 5,6,11,12-tetraphenyltetracene top
Crystal data top
C42H28Z = 4
Mr = 532.69F(000) = 1120
Orthorhombic, CmcaDx = 1.298 Mg m3
Hall symbol: -C 2bc 2Mo Kα radiation, λ = 0.7107 Å
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) ÅBlock, orange
V = 2726.52 (5) Å30.24 × 0.22 × 0.18 mm
Data collection top
SuperNova, Single source at offset, Atlas
diffractometer
7703 independent reflections
Radiation source: SuperNova (Mo) X-ray Source6070 reflections with > 3σ(I)
Mirror monochromatorRint = 0.033
Detector resolution: 10.3590 pixels mm-1θmax = 51.4°, θmin = 2.9°
ω scansh = 058
Absorption correction: analytical
?
k = 015
Tmin = 0.983, Tmax = 0.987l = 031
83536 measured reflections
Refinement top
Refinement on F2383 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.022 w2 = 1/[s2(Fo2)]
wR(F2) = 0.055(Δ/σ)max < 0.001
S = 1.49Δρmax = 0.18 e Å3
6070 reflectionsΔρmin = 0.18 e Å3
Crystal data top
C42H28V = 2726.52 (5) Å3
Mr = 532.69Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) Å0.24 × 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 = 0.987Rint = 0.033
83536 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.022383 parameters
wR(F2) = 0.0550 restraints
S = 1.49Δρmax = 0.18 e Å3
6070 reflectionsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
C(1)0.027310 (9)000.01
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)0.0927640.446050.1350210.028534*
H(5)0.046750.7006320.2119340.041594*
H(7)0.1317770.3345370.0311740.03803*
H(8)0.2185810.343210.0240270.03615*
H(9)0.2458740.142690.1578820.033709*
H(10)0.1831260.0664170.2369510.046305*
H(11)0.0954920.0654240.1832490.037348*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C(1)0.01000 (8)0.00907 (8)0.01081 (9)000.00128 (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)i1.4644 (5)C(6)—C(7)1.3978 (3)
C(1)—C(1)ii1.4644 (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)iii1.4263 (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)i1.4394 (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)i1.4229 (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)iii119.135 (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)iii119.135 (12)C(6)—C(7)—C(8)120.68 (2)
C(2)—C(1)—C(2)iii121.73 (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)i120.173 (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)i120.137 (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
C42H28Z = 4
Mr = 532.64F(000) = 1120
Orthorhombic, CmcaDx = 1.298 Mg m3
Hall symbol: -C 2bc 2Mo Kα radiation, λ = 0.7107 Å
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) ÅBlock, orange
V = 2726.52 (5) Å30.24 × 0.22 × 0.18 mm
Data collection top
SuperNova, Single source at offset, Atlas
diffractometer
7703 independent reflections
Radiation source: SuperNova (Mo) X-ray Source6070 reflections with > 3σ(I)
Mirror monochromatorRint = 0.033
Detector resolution: 10.3590 pixels mm-1θmax = 51.4°, θmin = 2.9°
ω scansh = 058
Absorption correction: analytical
?
k = 015
Tmin = 0.983, Tmax = 0.987l = 031
83536 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullThe 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 = 1.49Δρmax = 0.18 e Å3
6070 reflectionsΔρmin = 0.18 e Å3
383 parameters
Crystal data top
C42H28V = 2726.52 (5) Å3
Mr = 532.64Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) Å0.24 × 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 = 0.987Rint = 0.033
83536 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0220 restraints
wR(F2) = 0.055The 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 = 1.49Δρmax = 0.18 e Å3
6070 reflectionsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
C(1)0.027309 (10)000.01
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)0.0925310.4478650.1357650.031
H(5)0.0466370.7024140.2103670.034
H(7)0.1327930.3354480.0311350.033
H(8)0.2184560.3435940.0246440.04
H(9)0.245950.1389680.156420.043
H(10)0.1811340.0685060.236970.031
H(11)0.0947710.0630730.1817150.035
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C(1)0.01000 (8)0.00908 (9)0.01082 (9)000.00129 (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)0.0205280.0295860.0361050.0031290.0013350.006668
H(5)0.0350140.0240930.0381920.0060320.0031620.012973
H(7)0.0267330.0356660.0350400.0003670.0020140.014106
H(8)0.0229020.0384560.0528120.0081280.0052260.007858
H(9)0.0185210.0517080.0436010.0028170.0084750.002324
H(10)0.0298990.0561910.0328610.0023300.0087270.015203
H(11)0.0239890.0383640.0341770.0049240.0013710.013843
Geometric parameters (Å, º) top
C(1)—C(1)i1.4644 (5)C(6)—C(7)1.3978 (3)
C(1)—C(1)ii1.4644 (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)iii1.4263 (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)i1.4394 (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)i1.4229 (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)iii119.135 (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)iii119.135 (12)C(6)—C(7)—C(8)120.68 (2)
C(2)—C(1)—C(2)iii121.73 (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)i120.173 (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)i120.137 (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
C42H28Z = 4
Mr = 532.69F(000) = 1120
Orthorhombic, CmcaDx = 1.298 Mg m3
Hall symbol: -C 2bc 2Mo Kα radiation, λ = 0.7107 Å
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) ÅBlock, orange
V = 2726.52 (5) Å30.24 × 0.22 × 0.18 mm
Data collection top
SuperNova, Single source at offset, Atlas
diffractometer
7703 independent reflections
Radiation source: SuperNova (Mo) X-ray Source6070 reflections with > 3σ(I)
Mirror monochromatorRint = 0.033
Detector resolution: 10.3590 pixels mm-1θmax = 51.4°, θmin = 2.9°
ω scansh = 058
Absorption correction: analytical
?
k = 015
Tmin = 0.983, Tmax = 0.987l = 031
83536 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH 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 = 3.55Δρmax = 0.76 e Å3
6070 reflectionsΔρmin = 0.26 e Å3
96 parameters
Crystal data top
C42H28V = 2726.52 (5) Å3
Mr = 532.69Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) Å0.24 × 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 = 0.987Rint = 0.033
83536 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 3.55Δρmax = 0.76 e Å3
6070 reflectionsΔρmin = 0.26 e Å3
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
xyzUiso*/Ueq
C10.02728 (2)000.01
C20.053200 (15)0.14436 (6)0.04904 (3)0.01
C30.026877 (15)0.29592 (6)0.08760 (3)0.01
C40.052090 (17)0.44731 (6)0.13400 (3)0.013
C50.026493 (18)0.58999 (7)0.17554 (4)0.015
C60.107596 (15)0.13457 (6)0.07272 (3)0.011
C70.142874 (16)0.24868 (7)0.02855 (4)0.014
C80.192182 (17)0.25141 (8)0.05976 (4)0.019
C90.207010 (18)0.13937 (9)0.13455 (4)0.021
C100.17226 (2)0.02475 (9)0.17896 (4)0.02
C110.122828 (17)0.02348 (7)0.14825 (3)0.015
H40.0925150.4464020.1348910.0204
H50.0466890.7001470.2119410.034073
H70.1317390.3344640.0309210.029722
H80.2185720.3427280.0245430.023726
H90.245610.1425170.1576260.02009
H100.1831870.0660630.2366520.037264
H110.0956410.064760.1830280.029335
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.00965 (17)0.00890 (18)0.01039 (18)000.00083 (14)
C20.01055 (13)0.00978 (13)0.01052 (13)0.00087 (10)0.00008 (10)0.00107 (10)
C30.01236 (14)0.00912 (13)0.00994 (13)0.00090 (10)0.00021 (10)0.00096 (10)
C40.01517 (15)0.01149 (15)0.01325 (15)0.00303 (12)0.00085 (11)0.00274 (12)
C50.01880 (18)0.01130 (16)0.01484 (17)0.00225 (12)0.00060 (13)0.00340 (12)
C60.01076 (13)0.01153 (14)0.01150 (14)0.00103 (11)0.00013 (10)0.00116 (11)
C70.01264 (14)0.01359 (16)0.01721 (17)0.00177 (12)0.00236 (12)0.00047 (13)
C80.01155 (15)0.0200 (2)0.0244 (2)0.00268 (14)0.00280 (14)0.00282 (17)
C90.01217 (16)0.0271 (3)0.0234 (2)0.00003 (15)0.00289 (14)0.00476 (18)
C100.01707 (18)0.0265 (3)0.01651 (19)0.00197 (16)0.00484 (14)0.00070 (16)
C110.01472 (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)i1.4631 (10)C(6)—C(7)1.3985 (6)
C(1)—C(1)ii1.4631 (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)iii1.4270 (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)i1.4412 (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)i1.4206 (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)iii119.14 (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)iii119.14 (2)C(6)—C(7)—C(8)120.45 (5)
C(2)—C(1)—C(2)iii121.73 (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)i120.14 (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)i120.19 (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
C42H28Z = 4
Mr = 532.69F(000) = 1120
Orthorhombic, CmcaDx = 1.298 Mg m3
Hall symbol: -C 2bc 2Mo Kα radiation, λ = 0.7107 Å
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) ÅBlock, orange
V = 2726.52 (5) Å30.24 × 0.22 × 0.18 mm
Data collection top
SuperNova, Single source at offset, Atlas
diffractometer
7703 independent reflections
Radiation source: SuperNova (Mo) X-ray Source6070 reflections with > 3σ(I)
Mirror monochromatorRint = 0.033
Detector resolution: 10.3590 pixels mm-1θmax = 51.4°, θmin = 2.9°
ω scansh = 058
Absorption correction: analytical
?
k = 015
Tmin = 0.983, Tmax = 0.987l = 031
83536 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH 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 = 1.31Δρmax = 0.10 e Å3
3336 reflectionsΔρmin = 0.11 e Å3
96 parameters
Crystal data top
C42H28V = 2726.52 (5) Å3
Mr = 532.69Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) Å0.24 × 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 = 0.987Rint = 0.033
83536 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.068H atoms treated by a mixture of independent and constrained refinement
S = 1.31Δρmax = 0.10 e Å3
3336 reflectionsΔρmin = 0.11 e Å3
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
xyzUiso*/Ueq
C10.027328 (13)000.01
C20.053201 (9)0.14441 (4)0.048893 (19)0.011
C30.026851 (10)0.29589 (4)0.087626 (19)0.011
C40.052134 (12)0.44715 (5)0.13401 (2)0.014
C50.026519 (14)0.59000 (5)0.17553 (2)0.016
C60.107566 (10)0.13458 (4)0.07270 (2)0.012
C70.142859 (12)0.24873 (5)0.02864 (3)0.015
C80.192140 (13)0.25177 (7)0.05965 (4)0.019
C90.207169 (15)0.13945 (9)0.13451 (4)0.022
C100.172371 (17)0.02480 (8)0.17889 (3)0.021
C110.122846 (13)0.02348 (6)0.14833 (2)0.016
H40.0925580.4464010.1348920.0204
H50.0466960.7001850.2119530.034073
H70.1317460.3344070.0308820.029722
H80.2186090.3428540.0244940.023726
H90.245750.1425280.157710.02009
H100.1831850.0660480.2366430.037264
H110.0956360.0647760.1830340.029335
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.01049 (10)0.00959 (10)0.01119 (10)000.00114 (7)
C20.01116 (8)0.01034 (8)0.01145 (8)0.00077 (5)0.00004 (5)0.00119 (5)
C30.01282 (9)0.00982 (8)0.01093 (8)0.00082 (5)0.00022 (5)0.00120 (5)
C40.01567 (10)0.01224 (9)0.01433 (9)0.00271 (6)0.00107 (6)0.00314 (6)
C50.01931 (12)0.01188 (9)0.01584 (10)0.00206 (7)0.00070 (7)0.00391 (7)
C60.01143 (8)0.01235 (8)0.01221 (8)0.00131 (6)0.00028 (5)0.00067 (6)
C70.01276 (9)0.01490 (10)0.01808 (11)0.00166 (7)0.00198 (7)0.00084 (7)
C80.01218 (9)0.02048 (13)0.02547 (15)0.00258 (8)0.00223 (8)0.00180 (11)
C90.01315 (10)0.02777 (18)0.02376 (15)0.00033 (10)0.00319 (9)0.00407 (12)
C100.01737 (12)0.02763 (17)0.01737 (12)0.00134 (11)0.00496 (8)0.00131 (10)
C110.01526 (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)i1.4654 (7)C(6)—C(7)1.3982 (4)
C(1)—C(1)ii1.4654 (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)iii1.4257 (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)i1.4398 (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)i1.4220 (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)iii119.114 (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)iii119.114 (16)C(6)—C(7)—C(8)120.63 (4)
C(2)—C(1)—C(2)iii121.77 (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)i120.152 (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)i120.186 (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
C42H28Z = 4
Mr = 532.69F(000) = 1120
Orthorhombic, CmcaDx = 1.298 Mg m3
Hall symbol: -C 2bc 2Mo Kα radiation, λ = 0.7107 Å
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) ÅBlock, orange
V = 2726.52 (5) Å30.24 × 0.22 × 0.18 mm
Data collection top
SuperNova, Single source at offset, Atlas
diffractometer
7703 independent reflections
Radiation source: SuperNova (Mo) X-ray Source6070 reflections with > 3σ(I)
Mirror monochromatorRint = 0.033
Detector resolution: 10.3590 pixels mm-1θmax = 51.4°, θmin = 2.9°
ω scansh = 058
Absorption correction: analytical
?
k = 015
Tmin = 0.983, Tmax = 0.987l = 031
83536 measured reflections
Refinement top
Refinement on F0 restraints
Least-squares matrix: full4 constraints
wR(F2) = 0.033All H-atom parameters refined
S = 2.96w = 1/σ(F)
6289 reflections
159 parameters
Crystal data top
C42H28V = 2726.52 (5) Å3
Mr = 532.69Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.8106 (3) ŵ = 0.07 mm1
b = 7.1602 (1) ÅT = 100 K
c = 14.2029 (1) Å0.24 × 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 = 0.987Rint = 0.033
83536 measured reflections
Refinement top
wR(F2) = 0.033159 parameters
S = 2.960 restraints
6289 reflectionsAll 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
xyzUiso*/Ueq
C10.72268 (1)0.25000.50000.0095
C20.696799 (7)0.10557 (3)0.45103 (1)0.0100
C30.723158 (7)0.04588 (3)0.41238 (1)0.0102
C40.642450 (7)0.11542 (3)0.42731 (1)0.0110
C50.697892 (8)0.19713 (3)0.36602 (2)0.0130
C60.723472 (9)0.34000 (3)0.32450 (2)0.0146
C70.607131 (8)0.00143 (3)0.47135 (2)0.0143
C80.557894 (9)0.00162 (4)0.44038 (2)0.0184
C90.542865 (9)0.11067 (4)0.36546 (2)0.0205
C100.57771 (1)0.22543 (4)0.32111 (2)0.0198
C110.627169 (9)0.22650 (4)0.35169 (2)0.0151
H10.6577 (2)0.1986 (8)0.3641 (4)0.03
H20.7034 (2)0.4513 (8)0.2895 (5)0.04
H30.6182 (2)0.0840 (9)0.5297 (4)0.04
H40.5313 (2)0.0936 (9)0.4748 (5)0.04
H50.5042 (2)0.109 (1)0.3420 (5)0.04
H60.5673 (2)0.313 (1)0.2627 (5)0.05
H70.6542 (2)0.3130 (9)0.3181 (4)0.04
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0096 (3)0.0087 (3)0.0101 (3)0.000000 (1)0.000000 (1)0.0012 (2)
C20.0101 (2)0.0093 (2)0.0105 (2)0.0007 (2)0.0001 (2)0.0012 (2)
C30.0118 (2)0.0088 (2)0.0099 (2)0.0008 (2)0.0002 (2)0.0013 (2)
C40.0104 (2)0.0113 (2)0.0112 (2)0.0013 (2)0.0002 (2)0.0005 (2)
C50.0146 (3)0.0111 (3)0.0133 (3)0.0027 (2)0.0010 (2)0.0032 (2)
C60.0183 (3)0.0108 (3)0.0148 (3)0.0021 (2)0.0008 (2)0.0039 (2)
C70.0119 (2)0.0139 (3)0.0170 (3)0.0017 (2)0.0021 (2)0.0010 (2)
C80.0111 (3)0.0197 (4)0.0244 (4)0.0027 (2)0.0023 (2)0.0018 (3)
C90.0120 (3)0.0268 (4)0.0228 (4)0.0001 (3)0.0033 (3)0.0040 (3)
C100.0164 (3)0.0265 (4)0.0164 (3)0.0014 (3)0.0050 (3)0.0014 (3)
C110.0141 (3)0.0183 (3)0.0128 (3)0.0013 (2)0.0018 (2)0.0024 (2)
H10.02 (1)0.03 (1)0.04 (1)0.005 (8)0.003 (9)0.018 (9)
H20.03 (1)0.03 (1)0.05 (2)0.01 (1)0.00 (1)0.02 (1)
H30.03 (1)0.04 (1)0.04 (1)0.01 (1)0.01 (1)0.01 (1)
H40.02 (1)0.05 (1)0.06 (2)0.008 (9)0.01 (1)0.01 (1)
H50.03 (1)0.06 (2)0.04 (1)0.00 (1)0.01 (1)0.00 (1)
H60.05 (1)0.06 (2)0.03 (1)0.02 (1)0.01 (1)0.02 (1)
H70.02 (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 = 711.51F(000) = 2041.53
Monoclinic, C2/cDx = 1.624 Mg m3
Hall symbol: -C 2ycNeutron radiation, λ = 0.4-3.4 Å
a = 33.5759 (1) ÅCell parameters from 1000 reflections
b = 7.6607 (1) ŵ = 0.19 mm1
c = 25.1114 (2) ÅT = 100 K
β = 114.6982 (4)°Sphere, yellow
V = 5868.14 (7) Å30.6 mm (radius)
Data collection top
TOPAZ Single Crystal Diffractometer32750 measured reflections
Radiation source: spallation neutron source, SNS BL1225886 independent reflections
Not applicable to TOF Laue technique monochromator25886 reflections with > 3σ(I)
time–of–flight Laue scansh = 6566
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 = 159
Tmin = 0.747, Tmax = 0.888l = 4650
Refinement top
Refinement on F2All H-atom parameters refined
Least-squares matrix: fullWeighting scheme based on measured s.u.'s
R[F2 > 2σ(F2)] = 0.051(Δ/σ)max < 0.001
wR(F2) = 0.040Δρmax = 0.21 e Å3
S = 1.57Δρmin = 0.20 e Å3
25886 reflectionsExtinction correction: B-C Secondary type 1 Lorenzian
693 parametersExtinction coefficient: 2.71E-05 (6)
0 restraints
Crystal data top
2(C6H2N3O7)·C5H11NO2·2(C3H5N2)V = 5868.14 (7) Å3
Mr = 711.51Z = 8
Monoclinic, C2/cNeutron radiation, λ = 0.4-3.4 Å
a = 33.5759 (1) ŵ = 0.19 mm1
b = 7.6607 (1) ÅT = 100 K
c = 25.1114 (2) Å0.6 mm (radius)
β = 114.6982 (4)°
Data collection top
TOPAZ Single Crystal Diffractometer32750 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 = 0.88825886 reflections with > 3σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.040All H-atom parameters refined
S = 1.57Δρmax = 0.21 e Å3
25886 reflectionsΔρmin = 0.20 e Å3
693 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/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
U11U22U33U12U13U23
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 = 711.51Dx = 1.62 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2ycCell parameters from 37970 reflections
a = 33.5939 (5) Åθ = 2.8–57.9°
b = 7.66580 (8) ŵ = 0.14 mm1
c = 25.1324 (3) ÅT = 100 K
β = 114.7162 (17)°Block, yellow
V = 5879.29 (13) Å30.29 × 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 Source21277 reflections with > 3σ(I)
Mirror monochromatorRint = 0.035
Detector resolution: 10.3590 pixels mm-1θmax = 58.6°, θmin = 2.4°
ω scansh = 7379
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 = 1718
Tmin = 0.974, Tmax = 0.982l = 6060
165808 measured reflections
Refinement top
Refinement on F21306 parameters
Least-squares matrix: full1 restraint
R[F2 > 2σ(F2)] = 0.03 w2 = 1/[s2(Fo2)]
wR(F2) = 0.072(Δ/σ)max = 0.009
S = 0.87Δρmax = 0.31 e Å3
21277 reflectionsΔρmin = 0.26 e Å3
Crystal data top
2(C6H2N3O7)·C5H11NO2·2(C3H5N2)V = 5879.29 (13) Å3
Mr = 711.51Z = 8
Monoclinic, C2/cMo Kα radiation
a = 33.5939 (5) ŵ = 0.14 mm1
b = 7.66580 (8) ÅT = 100 K
c = 25.1324 (3) Å0.29 × 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 = 0.982Rint = 0.035
165808 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031306 parameters
wR(F2) = 0.0721 restraint
S = 0.87Δρmax = 0.31 e Å3
21277 reflectionsΔρmin = 0.26 e Å3
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
xyzUiso*/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)0.3806360.1539950.2703480.015
H(132)0.3566840.1829080.1925430.015
H(141)0.4565380.5164790.296040.026
H(142)0.4405170.3406990.3303630.026
H(143)0.4717590.2986720.2888670.026
H(151)0.3422910.4770750.2061740.034
H(152)0.3676040.4366670.2847320.034
H(153)0.385140.6124190.252530.034
H(161)0.4364610.332850.1849780.041
H(162)0.3804750.3997680.1491760.041
H(163)0.4207080.5545940.1924990.041
H(3A)0.3439450.1292430.195830.019
H(2A)0.2815170.248120.1036810.019
H(4A)0.3134990.0312550.2709540.022
H(5A)0.2255830.1297290.2223570.021
H(8A)0.0492510.5540260.0463180.015
H(10A)0.0923390.6996690.0860270.014
H(1A)0.2109770.2608990.1190560.017
H(1B)0.4238280.3512010.0536890.016
H(3B)0.4962650.0438960.2018290.019
H(2B)0.4189140.1730.1382320.018
H(4B)0.5021790.348940.0621850.019
H(5B)0.5505970.1376840.1588820.022
H(8B)0.2597780.608260.0336790.015
H(10B)0.3075060.7921850.1576770.015
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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 = 711.51Dx = 1.62 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2ycCell parameters from 37970 reflections
a = 33.5939 (5) Åθ = 2.8–57.9°
b = 7.66580 (8) ŵ = 0.14 mm1
c = 25.1324 (3) ÅT = 100 K
β = 114.7162 (17)°Block, yellow
V = 5879.29 (13) Å30.29 × 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 Source21277 reflections with > 3σ(I)
Mirror monochromatorRint = 0.035
Detector resolution: 10.3590 pixels mm-1θmax = 58.6°, θmin = 2.4°
ω scansh = 7379
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 = 1718
Tmin = 0.974, Tmax = 0.982l = 6060
165808 measured reflections
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullH 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 = 0.87Δρmax = 0.31 e Å3
21277 reflectionsΔρmin = 0.26 e Å3
1306 parameters
Crystal data top
2(C6H2N3O7)·C5H11NO2·2(C3H5N2)V = 5879.29 (13) Å3
Mr = 711.51Z = 8
Monoclinic, C2/cMo Kα radiation
a = 33.5939 (5) ŵ = 0.14 mm1
b = 7.66580 (8) ÅT = 100 K
c = 25.1324 (3) Å0.29 × 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 = 0.982Rint = 0.035
165808 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031 restraint
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 0.87Δρmax = 0.31 e Å3
21277 reflectionsΔρmin = 0.26 e Å3
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
xyzUiso*/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)0.3806360.1539950.2703480.015
H(132)0.3566840.1829080.1925430.015
H(141)0.4565380.5164790.296040.026
H(142)0.4405170.3406990.3303630.026
H(143)0.4717590.2986720.2888670.026
H(151)0.3422910.4770750.2061740.034
H(152)0.3676040.4366670.2847320.034
H(153)0.385140.6124190.252530.034
H(161)0.4364610.332850.1849780.041
H(162)0.3804750.3997680.1491760.041
H(163)0.4207080.5545940.1924990.041
H(3A)0.3439450.1292430.195830.019
H(2A)0.2815170.248120.1036810.019
H(4A)0.3134990.0312550.2709540.022
H(5A)0.2255830.1297290.2223570.021
H(8A)0.0492510.5540260.0463180.015
H(10A)0.0923390.6996690.0860270.014
H(1A)0.2109770.2608990.1190560.017
H(1B)0.4238280.3512010.0536890.016
H(3B)0.4962650.0438960.2018290.019
H(2B)0.4189140.1730.1382320.018
H(4B)0.5021790.348940.0621850.019
H(5B)0.5505970.1376840.1588820.022
H(8B)0.2597780.608260.0336790.015
H(10B)0.3075060.7921850.1576770.015
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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)0.0407870.0302700.0333580.0026260.0265430.000576
H(132)0.0215340.0304800.0316090.0036700.0044870.005556
H(141)0.0430510.0260260.0513050.0133990.0096730.006372
H(142)0.0422280.0543380.0210360.0054530.0118750.000770
H(143)0.0246810.0469480.0455000.0042710.0103120.013709
H(151)0.0341060.0464190.0488030.0132130.0079980.013075
H(152)0.0495230.0443970.0514250.0072120.0317510.001975
H(153)0.0490520.0206680.0667320.0033690.0186730.008672
H(161)0.0663340.0453270.0477560.0046350.0403950.006920
H(162)0.0671160.0539890.0229660.0022540.0030450.007358
H(163)0.0969030.0258870.0512470.0160330.0380390.002700
H(3A)0.0181620.0381540.0442300.0028310.0121370.000268
H(2A)0.0418330.0413040.0317520.0042680.0225200.012703
H(4A)0.0368050.0538090.0199790.0145310.0030880.010759
H(5A)0.0325700.0579580.0360110.0071250.0234740.007602
H(1A)0.0213440.0346220.0263950.0078450.0026170.005924
H(8A)0.0227810.0394490.0293460.0053750.0171600.004159
H(10A)0.0320160.0332480.0196410.0048240.0107540.011393
H(1B)0.0209010.0316900.0242870.0059260.0061780.009555
H(3B)0.0318870.0325250.0229990.0062700.0109720.011693
H(2B)0.0230340.0332840.0325120.0000480.0161870.004750
H(4B)0.0300580.0353330.0293880.0019860.0179770.010391
H(5B)0.0189740.0397980.0330440.0085580.0083330.007312
H(8B)0.0214870.0359740.0342300.0037140.0177340.006451
H(10B)0.0323730.0293150.0226730.0046640.0124280.010350
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 = 711.51Dx = 1.62 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2ycCell parameters from 37970 reflections
a = 33.5939 (5) Åθ = 2.8–57.9°
b = 7.66580 (8) ŵ = 0.14 mm1
c = 25.1324 (3) ÅT = 100 K
β = 114.7162 (17)°Block, yellow
V = 5879.29 (13) Å30.29 × 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 Source21277 reflections with > 3σ(I)
Mirror monochromatorRint = 0.035
Detector resolution: 10.3590 pixels mm-1θmax = 58.6°, θmin = 2.4°
ω scansh = 7379
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 = 1718
Tmin = 0.974, Tmax = 0.982l = 6060
165808 measured reflections
Refinement top
Refinement on F2451 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.051 w2 = 1/[s2(Fo2)]
wR(F2) = 0.127(Δ/σ)max < 0.001
S = 1.51Δρmax = 0.90 e Å3
21277 reflectionsΔρmin = 0.41 e Å3
Crystal data top
2(C6H2N3O7)·C5H11NO2·2(C3H5N2)V = 5879.29 (13) Å3
Mr = 711.51Z = 8
Monoclinic, C2/cMo Kα radiation
a = 33.5939 (5) ŵ = 0.14 mm1
b = 7.66580 (8) ÅT = 100 K
c = 25.1324 (3) Å0.29 × 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 = 0.982Rint = 0.035
165808 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051451 parameters
wR(F2) = 0.1270 restraints
S = 1.51Δρmax = 0.90 e Å3
21277 reflectionsΔρmin = 0.41 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/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)0.380620.1539230.2704510.014669
H(132)0.3566830.1829080.1925420.014669
H(141)0.4565670.5169040.2960480.025771
H(142)0.4405270.3407590.3303080.025771
H(143)0.4717980.2985430.288860.025771
H(151)0.3423280.4770810.2062240.033716
H(152)0.3676070.4367020.2847020.033716
H(153)0.385170.6127090.2525430.033716
H(161)0.4366430.3322210.1849650.040908
H(162)0.3806140.399850.1493430.040908
H(163)0.4207240.5548320.1925090.040908
H(3A)0.3438760.1292580.1958170.019295
H(2A)0.2815170.2481180.1036830.01897
H(4A)0.3134650.031360.2708840.022434
H(5A)0.2256220.1297420.222330.021491
H(8A)0.0491830.5540480.0463690.014542
H(10A)0.0923370.6996930.086040.01435
H(1A)0.2110110.2608410.1190920.017242
H(1B)0.4238490.3511490.0537160.016435
H(3B)0.4962550.043990.2017850.019383
H(2B)0.4188570.1729640.1382450.017586
H(4B)0.5021690.3488660.0622160.019446
H(5B)0.5505370.1377510.1588480.021574
H(8B)0.2597640.6082560.0336710.014973
H(10B)0.3075040.792210.1576910.015326
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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 = 711.51Dx = 1.62 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2ycCell parameters from 37970 reflections
a = 33.5939 (5) Åθ = 2.8–57.9°
b = 7.66580 (8) ŵ = 0.14 mm1
c = 25.1324 (3) ÅT = 100 K
β = 114.7162 (17)°Block, yellow
V = 5879.29 (13) Å30.29 × 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 Source21277 reflections with > 3σ(I)
Mirror monochromatorRint = 0.035
Detector resolution: 10.3590 pixels mm-1θmax = 58.6°, θmin = 2.4°
ω scansh = 7379
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 = 1718
Tmin = 0.974, Tmax = 0.982l = 6060
165808 measured reflections
Refinement top
Refinement on F2451 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.056 w2 = 1/[s2(Fo2)]
wR(F2) = 0.166(Δ/σ)max < 0.001
S = 0.8Δρmax = 0.19 e Å3
10569 reflectionsΔρmin = 0.21 e Å3
Crystal data top
2(C6H2N3O7)·C5H11NO2·2(C3H5N2)V = 5879.29 (13) Å3
Mr = 711.51Z = 8
Monoclinic, C2/cMo Kα radiation
a = 33.5939 (5) ŵ = 0.14 mm1
b = 7.66580 (8) ÅT = 100 K
c = 25.1324 (3) Å0.29 × 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 = 0.982Rint = 0.035
165808 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.056451 parameters
wR(F2) = 0.1660 restraints
S = 0.8Δρmax = 0.19 e Å3
10569 reflectionsΔρmin = 0.21 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/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)0.3806250.1539450.270420.014669
H(132)0.3566860.1829080.1925460.014669
H(141)0.456530.5163680.2960380.025771
H(142)0.4405050.3406260.3304310.025771
H(143)0.4717620.2986610.2888670.025771
H(151)0.3423280.4770810.2062230.033716
H(152)0.3675890.4365080.2848660.033716
H(153)0.3851320.612340.2525270.033716
H(161)0.4363960.3330520.1849820.040908
H(162)0.3803130.3996720.1489750.040908
H(163)0.4206710.5540670.1924770.040908
H(3A)0.3439450.1292430.195830.019295
H(2A)0.2815120.2480620.1037350.01897
H(4A)0.3135270.0311740.2710110.022434
H(5A)0.2255390.1297150.2223880.021491
H(8A)0.0492140.5540380.0463460.014542
H(10A)0.0923360.6997060.0860470.01435
H(1A)0.2109970.2608650.1190770.017242
H(1B)0.423840.3511710.0537050.016435
H(3B)0.4962570.0439680.2017960.019383
H(2B)0.4189640.1730320.138220.017586
H(4B)0.502170.348870.0622140.019446
H(5B)0.5506240.1376520.1588970.021574
H(8B)0.2597970.6082650.033690.014973
H(10B)0.3075090.7921330.1576510.015326
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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 formulaC42H28C42H28C42H28C42H28
Mr532.69532.69532.64532.69
Crystal system, space groupOrthorhombic, CmcaOrthorhombic, CmcaOrthorhombic, CmcaOrthorhombic, Cmca
Temperature (K)100100100100
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, 9090, 90, 9090, 90, 9090, 90, 90
V3)2724.01 (5)2726.52 (5)2726.52 (5)2726.52 (5)
Z4444
Radiation typeNeutron, λ = 0.4-3.4 ÅMo KαMo KαMo Kα
µ (mm1)0.200.070.070.07
Crystal size (mm)1.50 × 1.50 × 1.000.24 × 0.22 × 0.180.24 × 0.22 × 0.180.24 × 0.22 × 0.18
Data collection
DiffractometerTOPAZ Single Crystal DiffractometerSuperNova, Single source at offset, Atlas
diffractometer
SuperNova, Single source at offset, Atlas
diffractometer
SuperNova, Single source at offset, Atlas
diffractometer
Absorption correctionAnalytical
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
AnalyticalAnalyticalAnalytical
Tmin, Tmax0.646, 0.8480.983, 0.9870.983, 0.9870.983, 0.987
No. of measured, independent and
observed [ > 3σ(I)] reflections
24945, 22955, 22955 83536, 7703, 6070 83536, 7703, 6070 83536, 7703, 6070
Rint?0.0330.0330.033
Distance from source to specimen (mm)1.1001.1001.100
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 reflections22775607060706070
No. of parameters18238338396
No. of restraints0000
H-atom treatmentAll 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 Å3)0.23, 0.310.18, 0.180.18, 0.180.76, 0.26


(Rubrene_Xray_IAM_HO)(Rubrene_HAR)(BIPa_neutron_100K)(BIPa_X_multipole_model)
Crystal data
Chemical formulaC42H28C42H282(C6H2N3O7)·C5H11NO2·2(C3H5N2)2(C6H2N3O7)·C5H11NO2·2(C3H5N2)
Mr532.69532.69711.51711.51
Crystal system, space groupOrthorhombic, CmcaOrthorhombic, CmcaMonoclinic, C2/cMonoclinic, C2/c
Temperature (K)100100100100
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, 9090, 90, 9090, 114.6982 (4), 9090, 114.7162 (17), 90
V3)2726.52 (5)2726.52 (5)5868.14 (7)5879.29 (13)
Z4488
Radiation typeMo KαMo KαNeutron, λ = 0.4-3.4 ÅMo Kα
µ (mm1)0.070.070.190.14
Crystal size (mm)0.24 × 0.22 × 0.180.24 × 0.22 × 0.180.6 (radius)0.29 × 0.21 × 0.16
Data collection
DiffractometerSuperNova, Single source at offset, Atlas
diffractometer
SuperNova, Single source at offset, Atlas
diffractometer
TOPAZ Single Crystal DiffractometerSuperNova, Single source at offset, Atlas
diffractometer
Absorption correctionAnalyticalAnalyticalAnalytical
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, Tmax0.983, 0.9870.983, 0.9870.747, 0.8880.974, 0.982
No. of measured, independent and
observed [ > 3σ(I)] reflections
83536, 7703, 6070 83536, 7703, 6070 32750, 25886, 25886 165808, 27262, 21277
Rint0.0330.033?0.035
Distance from source to specimen (mm)1.1001.1001.201
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 reflections333662892588621277
No. of parameters961596931306
No. of restraints0001
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementAll H-atom parameters refinedAll H-atom parameters refined?
Δρmax, Δρmin (e Å3)0.10, 0.11?, ?0.21, 0.200.31, 0.26


(BIPa_X_MM_Shade)(BIPa_Xray_IAM)(BIPa_X_HO_IAM)
Crystal data
Chemical formula2(C6H2N3O7)·C5H11NO2·2(C3H5N2)2(C6H2N3O7)·C5H11NO2·2(C3H5N2)2(C6H2N3O7)·C5H11NO2·2(C3H5N2)
Mr711.51711.51711.51
Crystal system, space groupMonoclinic, C2/cMonoclinic, C2/cMonoclinic, C2/c
Temperature (K)100100100
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), 9090, 114.7162 (17), 9090, 114.7162 (17), 90
V3)5879.29 (13)5879.29 (13)5879.29 (13)
Z888
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.140.140.14
Crystal size (mm)0.29 × 0.21 × 0.160.29 × 0.21 × 0.160.29 × 0.21 × 0.16
Data collection
DiffractometerSuperNova, Single source at offset, Atlas
diffractometer
SuperNova, Single source at offset, Atlas
diffractometer
SuperNova, Single source at offset, Atlas
diffractometer
Absorption correctionGaussian
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, Tmax0.974, 0.9820.974, 0.9820.974, 0.982
No. of measured, independent and
observed [ > 3σ(I)] reflections
165808, 27262, 21277 165808, 27262, 21277 165808, 27262, 21277
Rint0.0350.0350.035
Distance from source to specimen (mm)1.2011.2011.201
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 reflections212772127710569
No. of parameters1306451451
No. of restraints100
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement??
Δρmax, Δρmin (e Å3)0.31, 0.260.90, 0.410.19, 0.21

Computer programs: CrystalPlan (Zikovsky, J. et al. 2011), CrysAlis PRO, Agilent Technologies Version 1.171.36.28, CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44), MANTID (Taylor, J. et al. 2012) & ANVRED2X (local program), SHELXS97 (Sheldrick, 2008), GSAS (Larson & Von Dreele, 2004), SHELXL97 (Sheldrick, 2008), Volkov et al., (2006), XD2006 (Volkov et al., 2006).

Selected geometric parameters (Å, º) for (Rubrene_Xray_multipolemodel) top
C(1)—C(1)i1.4644 (5)C(6)—C(7)1.3978 (3)
C(1)—C(1)ii1.4644 (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)iii1.4263 (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)i1.4394 (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)i1.4229 (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)iii119.135 (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)iii119.135 (12)C(6)—C(7)—C(8)120.68 (2)
C(2)—C(1)—C(2)iii121.73 (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)i120.173 (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)i120.137 (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) top
C(1)—C(1)i1.4644 (5)C(6)—C(7)1.3978 (3)
C(1)—C(1)ii1.4644 (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)iii1.4263 (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)i1.4394 (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)i1.4229 (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)iii119.135 (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)iii119.135 (12)C(6)—C(7)—C(8)120.68 (2)
C(2)—C(1)—C(2)iii121.73 (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)i120.173 (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)i120.137 (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) top
C(1)—C(1)i1.4631 (10)C(6)—C(7)1.3985 (6)
C(1)—C(1)ii1.4631 (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)iii1.4270 (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)i1.4412 (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)i1.4206 (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)iii119.14 (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)iii119.14 (2)C(6)—C(7)—C(8)120.45 (5)
C(2)—C(1)—C(2)iii121.73 (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)i120.14 (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)i120.19 (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) top
C(1)—C(1)i1.4654 (7)C(6)—C(7)1.3982 (4)
C(1)—C(1)ii1.4654 (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)iii1.4257 (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)i1.4398 (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)i1.4220 (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)iii119.114 (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)iii119.114 (16)C(6)—C(7)—C(8)120.63 (4)
C(2)—C(1)—C(2)iii121.77 (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)i120.152 (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)i120.186 (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) 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)
Selected geometric parameters (Å, º) for (BIPa_X_MM_Shade) 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)
Selected geometric parameters (Å, º) for (BIPa_Xray_IAM) 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)
Selected geometric parameters (Å, º) for (BIPa_X_HO_IAM) 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)
 

Follow Acta Cryst. A
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds