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In the title co-crystal, C10H11NO2·C10H13NO2, the carboxyl­ic acid moiety uses its acid H atom as the donor atom to bind strongly to the negatively charged O atom of the zwitterionic moiety [O...O = 2.557 (2) Å]. Meanwhile, the protonated N atom of the zwitterionic moiety forms a hydrogen bond with the double-bonded O atom of an adjacent zwitterionic moiety [N...O = 2.703 (2) Å] to give rise to a linear chain motif. The butenyl substituent (on the zwitterion) is disordered with respect to a butyl group and the butyl substituent (on the neutral mol­ecule) is disordered with respect to a butenyl group, the site occupancy for both being in an approximate 0.6:0.4 ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012675/rz6069sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012675/rz6069Isup2.hkl
Contains datablock I

CCDC reference: 272102

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.063
  • wR factor = 0.229
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C9
Author Response: The structure is disordered in the butenyl/butyl groups.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C9'
Author Response: The structure is disordered in the butenyl/butyl groups.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H7C
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H7D
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H8C
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H8D
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H9C
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H9D
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H10C
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H10D
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H10E
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H18C
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H18D
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H19'
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H20D
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H20E
Author Response: CHECKCIF incorrectly detected isolated hydrogen atoms. There are no isolated atoms.

Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.59 Ratio PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.70 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.36 Ratio PLAT326_ALERT_2_B Check for Possibly Missing H on sp3? Carbon .... <C7'
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.36 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
Author Response: The structure is disordered in the butenyl/butyl groups.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
Author Response: The structure is disordered in the butenyl/butyl groups.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
Author Response: The structure is disordered in the butenyl/butyl groups.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
Author Response: The structure is disordered in the butenyl/butyl groups.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
Author Response: The structure is disordered in the butenyl/butyl groups.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C19'
Author Response: The structure is disordered in the butenyl/butyl groups.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.34
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.83
PLAT301_ALERT_3_C Main Residue  Disorder .........................      24.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C4     -   C5     ...       1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C5     -   C6     ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C14    -   C15    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C15    -   C16    ...       1.38 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.860(10) ......       3.00 su-Rat
              O3   -H3O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.860(10) ......       3.00 su-Rat
              O3   -H3O     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.71(3), Rep   1.710(10) ......       3.00 su-Rat
              H3O  -O1      1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10.01 H12.22 N O2

16 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 20 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 31 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

5-(But-3-enyl)pyridinium-2-carboxylate–5-butylpyridine-2-carboxylic acid (1/1) top
Crystal data top
C10H11NO2·C10H13NO2F(000) = 760
Mr = 356.41Dx = 1.174 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 827 reflections
a = 12.010 (2) Åθ = 2.5–26.2°
b = 10.401 (1) ŵ = 0.08 mm1
c = 16.988 (2) ÅT = 295 K
β = 108.178 (2)°Block, colorless
V = 2016.2 (4) Å30.48 × 0.45 × 0.29 mm
Z = 4
Data collection top
Bruker SMART 1K area-detector
diffractometer
2231 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 26.9°, θmin = 1.8°
φ and ω scansh = 1514
13186 measured reflectionsk = 1213
4315 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.229H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.1215P)2 + 0.3711P]
where P = (Fo2 + 2Fc2)/3
4315 reflections(Δ/σ)max = 0.001
275 parametersΔρmax = 0.31 e Å3
126 restraintsΔρmin = 0.20 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.8342 (2)0.7036 (2)0.7947 (1)0.0810 (6)
O20.8037 (2)0.9156 (2)0.7948 (1)0.0855 (6)
O31.0363 (2)0.6638 (2)0.8995 (1)0.0870 (7)
O41.0984 (2)0.8641 (2)0.9213 (2)0.1094 (8)
N10.6300 (2)0.6645 (2)0.6789 (1)0.0574 (5)
N21.2297 (2)0.5738 (2)1.0119 (1)0.0864 (7)
C10.7771 (2)0.8055 (2)0.7704 (1)0.0639 (7)
C20.6614 (2)0.7862 (2)0.7024 (1)0.0563 (6)
C30.5872 (2)0.8835 (2)0.6627 (2)0.0688 (7)
C40.4858 (2)0.8541 (2)0.5995 (2)0.0716 (7)
C50.4559 (2)0.7278 (2)0.5753 (1)0.0649 (7)
C60.5320 (2)0.6332 (2)0.6182 (1)0.0621 (6)
C70.352 (1)0.696 (4)0.5009 (8)0.078 (2)0.587 (5)
C80.2373 (9)0.685 (2)0.5185 (5)0.104 (3)0.587 (5)
C90.1348 (5)0.6544 (8)0.4423 (5)0.102 (2)0.587 (5)
C100.0268 (7)0.679 (1)0.4439 (7)0.203 (5)0.587 (5)
C7'0.341 (2)0.690 (6)0.5120 (12)0.078 (2)0.41
C8'0.243 (1)0.691 (3)0.5486 (10)0.104 (3)0.41
C9'0.1234 (9)0.666 (1)0.4872 (5)0.102 (2)0.41
C10'0.093 (1)0.635 (2)0.3982 (6)0.203 (5)0.41
C111.1117 (2)0.7510 (2)0.93556 (16)0.0682 (7)
C121.2191 (2)0.7003 (2)1.00000 (15)0.0651 (7)
C131.2998 (3)0.7848 (3)1.04781 (19)0.0901 (9)
C141.3962 (3)0.7379 (4)1.1090 (2)0.102 (1)
C151.4103 (2)0.6079 (3)1.12272 (17)0.0860 (9)
C161.3228 (3)0.5321 (3)1.07149 (19)0.10 (1)
C171.5098 (8)0.5467 (11)1.1897 (7)0.099 (5)0.592 (6)
C181.6265 (9)0.5698 (11)1.1780 (7)0.147 (5)0.592 (6)
C191.7225 (8)0.5221 (12)1.2521 (6)0.176 (4)0.592 (6)
C201.8077 (12)0.4404 (17)1.2292 (11)0.242 (6)0.592 (6)
C17'1.5171 (13)0.555 (2)1.1876 (10)0.14 (1)0.413 (5)
C18'1.6059 (13)0.5003 (16)1.1516 (11)0.147 (5)0.41
C19'1.7094 (11)0.4344 (19)1.2116 (10)0.176 (4)0.41
C20'1.8002 (16)0.509 (2)1.2530 (17)0.242 (6)0.41
H3o0.9714 (19)0.688 (4)0.8637 (17)0.14 (1)*
H1n0.6771 (18)0.6052 (18)0.7034 (13)0.07 (1)*
H30.60520.96860.67840.083*
H40.43660.92040.57260.086*
H60.51490.54730.60470.074*
H7a0.34420.76130.45910.093*0.587 (5)
H7b0.36690.61470.47780.093*0.587 (5)
H8a0.22180.76550.54200.124*0.587 (5)
H8b0.24360.61820.55950.124*0.587 (5)
H90.14720.61930.39540.122*0.587 (5)
H10a0.01540.71390.49110.244*0.587 (5)
H10b0.03730.66070.39780.244*0.587 (5)
H7c0.32360.75020.46590.093*0.408 (6)
H7d0.34860.60530.49080.093*0.408 (6)
H8c0.24150.77360.57470.124*0.408 (6)
H8d0.25820.62580.59150.124*0.408 (6)
H9c0.09030.59730.51120.122*0.408 (6)
H9d0.07770.74240.48970.122*0.408 (6)
H10c0.00920.62710.37500.305*0.408 (6)
H10d0.12900.55500.39170.305*0.408 (6)
H10e0.12010.70190.37010.305*0.408 (6)
H131.28970.87281.03910.108*
H141.45180.79471.14120.122*
H161.32990.44371.07960.119*
H17a1.51080.58091.24300.119*0.592 (6)
H17b1.49620.45481.19020.119*0.592 (6)
H18a1.63680.66101.17060.176*0.592 (6)
H18b1.63030.52541.12870.176*0.592 (6)
H19a1.76320.59521.28370.212*0.592 (6)
H19b1.68810.47331.28740.212*0.592 (6)
H20a1.86750.41291.27840.363*0.592 (6)
H20b1.84290.48851.19490.363*0.592 (6)
H20c1.76840.36651.19930.363*0.592 (6)
H17c1.55340.62401.22570.168*0.413 (5)
H17d1.49280.48921.21890.168*0.413 (5)
H18c1.63490.56921.12480.176*0.413 (5)
H18d1.56660.43891.10900.176*0.413 (5)
H19'1.71050.34591.21960.212*0.413 (5)
H20d1.79730.59691.24410.291*0.413 (5)
H20e1.86590.47161.29070.291*0.413 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.076 (1)0.045 (1)0.085 (1)0.003 (1)0.028 (1)0.002 (1)
O20.091 (1)0.041 (1)0.089 (1)0.009 (1)0.022 (1)0.003 (1)
O30.072 (1)0.052 (1)0.099 (1)0.002 (1)0.027 (1)0.001 (1)
O40.088 (1)0.054 (1)0.144 (2)0.000 (1)0.026 (1)0.019 (1)
N10.059 (1)0.036 (1)0.061 (1)0.001 (1)0.006 (1)0.002 (1)
N20.075 (1)0.057 (1)0.095 (2)0.006 (1)0.020 (1)0.000 (1)
C10.065 (1)0.042 (1)0.063 (1)0.004 (1)0.011 (1)0.002 (1)
C20.059 (1)0.038 (1)0.057 (1)0.001 (1)0.003 (1)0.000 (1)
C30.073 (2)0.037 (1)0.075 (2)0.003 (1)0.009 (1)0.001 (1)
C40.068 (2)0.047 (1)0.076 (2)0.008 (1)0.011 (1)0.005 (1)
C50.060 (1)0.053 (1)0.063 (1)0.002 (1)0.006 (1)0.000 (1)
C60.062 (1)0.043 (1)0.065 (1)0.003 (1)0.004 (1)0.004 (1)
C70.066 (3)0.070 (3)0.076 (3)0.003 (3)0.009 (2)0.006 (5)
C80.066 (2)0.129 (4)0.095 (8)0.010 (2)0.005 (4)0.001 (8)
C90.070 (3)0.115 (4)0.113 (6)0.006 (2)0.018 (4)0.016 (5)
C100.127 (7)0.26 (1)0.182 (9)0.036 (7)0.005 (5)0.039 (8)
C7'0.066 (3)0.070 (3)0.076 (3)0.003 (3)0.009 (2)0.006 (5)
C8'0.066 (2)0.129 (4)0.095 (8)0.010 (2)0.005 (4)0.001 (8)
C9'0.070 (3)0.115 (4)0.113 (6)0.006 (2)0.018 (4)0.016 (5)
C10'0.127 (7)0.26 (1)0.182 (9)0.036 (7)0.005 (5)0.039 (8)
C110.063 (2)0.049 (2)0.078 (2)0.002 (1)0.001 (1)0.002 (1)
C120.057 (1)0.055 (2)0.071 (2)0.002 (1)0.001 (1)0.001 (1)
C130.073 (2)0.063 (2)0.111 (2)0.012 (1)0.005 (2)0.003 (2)
C140.068 (2)0.096 (3)0.110 (2)0.019 (1)0.017 (2)0.005 (2)
C150.060 (2)0.096 (2)0.085 (2)0.004 (2)0.003 (1)0.010 (2)
C160.086 (2)0.068 (2)0.110 (2)0.011 (2)0.020 (2)0.010 (2)
C170.085 (9)0.104 (8)0.089 (10)0.004 (6)0.001 (6)0.015 (6)
C180.074 (5)0.184 (12)0.161 (9)0.028 (7)0.007 (4)0.055 (8)
C190.083 (4)0.233 (13)0.182 (10)0.062 (7)0.003 (5)0.020 (7)
C200.204 (8)0.265 (18)0.216 (13)0.14 (1)0.005 (7)0.024 (10)
C17'0.058 (10)0.22 (2)0.110 (18)0.047 (11)0.016 (9)0.037 (15)
C18'0.074 (5)0.184 (12)0.161 (9)0.028 (7)0.007 (4)0.055 (8)
C19'0.083 (4)0.233 (13)0.182 (10)0.062 (7)0.003 (5)0.020 (7)
C20'0.204 (8)0.265 (18)0.216 (13)0.141 (10)0.005 (7)0.024 (10)
Geometric parameters (Å, º) top
O1—C11.260 (3)C4—H40.93
O2—C11.226 (3)C6—H60.93
O3—C111.293 (3)C7—H7a0.97
O4—C111.201 (3)C7—H7b0.97
N1—C61.341 (3)C8—H8a0.97
N1—C21.346 (3)C8—H8b0.97
N2—C161.326 (3)C9—H90.93
N2—C121.332 (3)C10—H10a0.93
C1—C21.519 (3)C10—H10b0.93
C2—C31.377 (3)C7'—H7c0.97
C3—C41.383 (3)C7'—H7d0.97
C4—C51.390 (3)C8'—H8c0.97
C5—C61.385 (3)C8'—H8d0.97
C5—C7'1.510 (5)C9'—H9c0.97
C5—C71.513 (4)C9'—H9d0.97
C7—C81.498 (4)C10'—H10c0.96
C8—C91.516 (5)C10'—H10d0.96
C9—C101.330 (5)C10'—H10e0.96
C7'—C8'1.499 (5)C13—H130.93
C8'—C9'1.508 (5)C14—H140.93
C9'—C10'1.477 (5)C16—H160.93
C11—C121.503 (3)C17—H17a0.97
C12—C131.371 (4)C17—H17b0.97
C13—C141.381 (4)C18—H18a0.97
C14—C151.374 (4)C18—H18b0.97
C15—C161.383 (4)C19—H19a0.97
C15—C17'1.508 (5)C19—H19b0.97
C15—C171.509 (4)C20—H20a0.96
C17—C181.495 (5)C20—H20b0.96
C18—C191.502 (5)C20—H20c0.96
C19—C201.473 (5)C17'—H17c0.97
C17'—C18'1.499 (5)C17'—H17d0.97
C18'—C19'1.504 (5)C18'—H18c0.97
C19'—C20'1.341 (5)C18'—H18d0.97
O3—H3o0.86 (1)C19'—H19'0.93
N1—H1n0.85 (1)C20'—H20d0.93
C3—H30.93C20'—H20e0.93
C6—N1—C2123.6 (2)H10a—C10—H10b120.0
C16—N2—C12117.2 (2)C8'—C7'—H7c109.3
O2—C1—O1128.1 (2)C5—C7'—H7c109.3
O2—C1—C2117.5 (2)C8'—C7'—H7d109.3
O1—C1—C2114.4 (2)C5—C7'—H7d109.3
N1—C2—C3117.9 (2)H7c—C7'—H7d108.0
N1—C2—C1117.1 (2)C7'—C8'—H8c108.6
C3—C2—C1125.0 (2)C9'—C8'—H8c108.6
C2—C3—C4119.7 (2)C7'—C8'—H8d108.6
C3—C4—C5121.5 (2)C9'—C8'—H8d108.6
C6—C5—C4116.6 (2)H8c—C8'—H8d107.6
C6—C5—C7'120 (3)C10'—C9'—H9c105.1
C4—C5—C7'123 (2)C8'—C9'—H9c105.1
C6—C5—C7121 (2)C10'—C9'—H9d105.1
C4—C5—C7122 (2)C8'—C9'—H9d105.1
N1—C6—C5120.7 (2)H9c—C9'—H9d105.9
C8—C7—C5114.9 (8)C9'—C10'—H10c109.5
C7—C8—C9113.3 (6)C9'—C10'—H10d109.5
C10—C9—C8118.6 (9)H10c—C10'—H10d109.5
C8'—C7'—C5112 (1)C9'—C10'—H10e109.5
C7'—C8'—C9'115 (1)H10c—C10'—H10e109.5
C10'—C9'—C8'129 (1)H10d—C10'—H10e109.5
O4—C11—O3124.2 (2)C12—C13—H13120.3
O4—C11—C12121.4 (2)C14—C13—H13120.3
O3—C11—C12114.4 (2)C15—C14—H14119.8
N2—C12—C13121.8 (2)C13—C14—H14119.8
N2—C12—C11118.5 (2)N2—C16—H16117.0
C13—C12—C11119.6 (2)C15—C16—H16117.0
C12—C13—C14119.5 (3)C18—C17—H17a109.0
C15—C14—C13120.3 (3)C15—C17—H17a109.0
C14—C15—C16115.2 (2)C18—C17—H17b109.0
C14—C15—C17'121 (1)C15—C17—H17b109.0
C16—C15—C17'124 (1)H17a—C17—H17b107.8
C14—C15—C17124.7 (5)C17—C18—H18a109.7
C16—C15—C17120.1 (5)C19—C18—H18a109.7
N2—C16—C15126.1 (3)C17—C18—H18b109.7
C18—C17—C15112.7 (7)C19—C18—H18b109.7
C17—C18—C19110.0 (8)H18a—C18—H18b108.2
C20—C19—C18113 (1)C20—C19—H19a109.1
C18'—C17'—C15113 (1)C18—C19—H19a109.1
C17'—C18'—C19'116 (1)C20—C19—H19b109.1
C20'—C19'—C18'117 (2)C18—C19—H19b109.1
C11—O3—H3o118 (3)H19a—C19—H19b107.8
C6—N1—H1n119 (2)C19—C20—H20a109.5
C2—N1—H1n117 (2)C19—C20—H20b109.5
C2—C3—H3120.1H20a—C20—H20b109.5
C4—C3—H3120.1C19—C20—H20c109.5
C3—C4—H4119.3H20a—C20—H20c109.5
C5—C4—H4119.3H20b—C20—H20c109.5
N1—C6—H6119.7C18'—C17'—H17c109.0
C5—C6—H6119.7C15—C17'—H17c109.0
C8—C7—H7a108.5C18'—C17'—H17d109.0
C5—C7—H7a108.5C15—C17'—H17d109.0
C8—C7—H7b108.5H17c—C17'—H17d107.8
C5—C7—H7b108.5C17'—C18'—H18c108.2
H7a—C7—H7b107.5C19'—C18'—H18c108.2
C7—C8—H8a108.9C17'—C18'—H18d108.2
C9—C8—H8a108.9C19'—C18'—H18d108.2
C7—C8—H8b108.9H18c—C18'—H18d107.4
C9—C8—H8b108.9C20'—C19'—H19'121.4
H8a—C8—H8b107.7C18'—C19'—H19'121.4
C10—C9—H9120.7C19'—C20'—H20d120.0
C8—C9—H9120.7C19'—C20'—H20e120.0
C9—C10—H10a120.0H20d—C20'—H20e120.0
C9—C10—H10b120.0
C6—N1—C2—C31.3 (4)C16—N2—C12—C130.8 (5)
C6—N1—C2—C1178.2 (2)C16—N2—C12—C11177.2 (3)
O2—C1—C2—N1176.8 (2)O4—C11—C12—N2178.8 (3)
O1—C1—C2—N13.4 (3)O3—C11—C12—N22.6 (4)
O2—C1—C2—C33.8 (4)O4—C11—C12—C134.8 (4)
O1—C1—C2—C3176.0 (2)O3—C11—C12—C13173.8 (3)
N1—C2—C3—C41.6 (4)N2—C12—C13—C141.3 (5)
C1—C2—C3—C4177.8 (2)C11—C12—C13—C14177.6 (3)
C2—C3—C4—C50.7 (4)C12—C13—C14—C150.9 (5)
C3—C4—C5—C60.7 (4)C13—C14—C15—C160.1 (5)
C3—C4—C5—C7'174 (1)C13—C14—C15—C17'178 (1)
C3—C4—C5—C7174.0 (7)C13—C14—C15—C17177.8 (7)
C2—N1—C6—C50.1 (4)C12—N2—C16—C150.0 (5)
C4—C5—C6—N11.1 (4)C14—C15—C16—N20.4 (6)
C7'—C5—C6—N1175.1 (9)C17'—C15—C16—N2178 (1)
C7—C5—C6—N1173.6 (7)C17—C15—C16—N2178.4 (7)
C6—C5—C7—C899 (3)C14—C15—C17—C1864 (1)
C4—C5—C7—C887 (3)C16—C15—C17—C18118.0 (8)
C5—C7—C8—C9179 (2)C15—C17—C18—C19172.5 (9)
C7—C8—C9—C10161 (2)C17—C18—C19—C20131 (1)
C6—C5—C7'—C8'96 (4)C14—C15—C17'—C18'103 (2)
C4—C5—C7'—C8'78 (4)C16—C15—C17'—C18'75 (2)
C5—C7'—C8'—C9'175 (3)C15—C17'—C18'—C19'174 (2)
C7'—C8'—C9'—C10'4 (5)C17'—C18'—C19'—C20'85 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3o···O10.86 (1)1.71 (1)2.557 (2)168 (4)
N1—H1n···O2i0.85 (1)1.98 (2)2.703 (2)141 (2)
Symmetry code: (i) x+3/2, y1/2, z+3/2.
 

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