Acta Crystallographica Section E
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Section E CRYSTALLOGRAPHIC COMMUNICATIONS

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5-(But-3-enyl)pyridinium-2-carboxylate–5-butylpyridine-2-carboxylic acid (1/1), a co-crystal from Fusarium moniliforme

J. Wang, G.-W. Li, Y.-C. Lin, S.-N. Zhou and S. W. Ng

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012675/rz6069sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012675/rz6069Isup2.hkl Contains datablock I

CCDC reference: 272102

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (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·C₁₀H₁₃NO₂	F(000) = 760
M_r = 356.41	D_x = 1.174 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 827 reflections
a = 12.010 (2) Å	θ = 2.5–26.2°
b = 10.401 (1) Å	µ = 0.08 mm⁻¹
c = 16.988 (2) Å	T = 295 K
β = 108.178 (2)°	Block, colorless
V = 2016.2 (4) Å³	0.48 × 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 tube	R_int = 0.027
Graphite monochromator	θ_max = 26.9°, θ_min = 1.8°
φ and ω scans	h = −15→14
13186 measured reflections	k = −12→13
4315 independent reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.229	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.1215P)² + 0.3711P] where P = (F_o² + 2F_c²)/3
4315 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.31 e Å⁻³
126 restraints	Δρ_min = −0.20 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.8342 (2)	0.7036 (2)	0.7947 (1)	0.0810 (6)
O2	0.8037 (2)	0.9156 (2)	0.7948 (1)	0.0855 (6)
O3	1.0363 (2)	0.6638 (2)	0.8995 (1)	0.0870 (7)
O4	1.0984 (2)	0.8641 (2)	0.9213 (2)	0.1094 (8)
N1	0.6300 (2)	0.6645 (2)	0.6789 (1)	0.0574 (5)
N2	1.2297 (2)	0.5738 (2)	1.0119 (1)	0.0864 (7)
C1	0.7771 (2)	0.8055 (2)	0.7704 (1)	0.0639 (7)
C2	0.6614 (2)	0.7862 (2)	0.7024 (1)	0.0563 (6)
C3	0.5872 (2)	0.8835 (2)	0.6627 (2)	0.0688 (7)
C4	0.4858 (2)	0.8541 (2)	0.5995 (2)	0.0716 (7)
C5	0.4559 (2)	0.7278 (2)	0.5753 (1)	0.0649 (7)
C6	0.5320 (2)	0.6332 (2)	0.6182 (1)	0.0621 (6)
C7	0.352 (1)	0.696 (4)	0.5009 (8)	0.078 (2)	0.587 (5)
C8	0.2373 (9)	0.685 (2)	0.5185 (5)	0.104 (3)	0.587 (5)
C9	0.1348 (5)	0.6544 (8)	0.4423 (5)	0.102 (2)	0.587 (5)
C10	0.0268 (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
C11	1.1117 (2)	0.7510 (2)	0.93556 (16)	0.0682 (7)
C12	1.2191 (2)	0.7003 (2)	1.00000 (15)	0.0651 (7)
C13	1.2998 (3)	0.7848 (3)	1.04781 (19)	0.0901 (9)
C14	1.3962 (3)	0.7379 (4)	1.1090 (2)	0.102 (1)
C15	1.4103 (2)	0.6079 (3)	1.12272 (17)	0.0860 (9)
C16	1.3228 (3)	0.5321 (3)	1.07149 (19)	0.10 (1)
C17	1.5098 (8)	0.5467 (11)	1.1897 (7)	0.099 (5)	0.592 (6)
C18	1.6265 (9)	0.5698 (11)	1.1780 (7)	0.147 (5)	0.592 (6)
C19	1.7225 (8)	0.5221 (12)	1.2521 (6)	0.176 (4)	0.592 (6)
C20	1.8077 (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
H3o	0.9714 (19)	0.688 (4)	0.8637 (17)	0.14 (1)*
H1n	0.6771 (18)	0.6052 (18)	0.7034 (13)	0.07 (1)*
H3	0.6052	0.9686	0.6784	0.083*
H4	0.4366	0.9204	0.5726	0.086*
H6	0.5149	0.5473	0.6047	0.074*
H7a	0.3442	0.7613	0.4591	0.093*	0.587 (5)
H7b	0.3669	0.6147	0.4778	0.093*	0.587 (5)
H8a	0.2218	0.7655	0.5420	0.124*	0.587 (5)
H8b	0.2436	0.6182	0.5595	0.124*	0.587 (5)
H9	0.1472	0.6193	0.3954	0.122*	0.587 (5)
H10a	0.0154	0.7139	0.4911	0.244*	0.587 (5)
H10b	−0.0373	0.6607	0.3978	0.244*	0.587 (5)
H7c	0.3236	0.7502	0.4659	0.093*	0.408 (6)
H7d	0.3486	0.6053	0.4908	0.093*	0.408 (6)
H8c	0.2415	0.7736	0.5747	0.124*	0.408 (6)
H8d	0.2582	0.6258	0.5915	0.124*	0.408 (6)
H9c	0.0903	0.5973	0.5112	0.122*	0.408 (6)
H9d	0.0777	0.7424	0.4897	0.122*	0.408 (6)
H10c	0.0092	0.6271	0.3750	0.305*	0.408 (6)
H10d	0.1290	0.5550	0.3917	0.305*	0.408 (6)
H10e	0.1201	0.7019	0.3701	0.305*	0.408 (6)
H13	1.2897	0.8728	1.0391	0.108*
H14	1.4518	0.7947	1.1412	0.122*
H16	1.3299	0.4437	1.0796	0.119*
H17a	1.5108	0.5809	1.2430	0.119*	0.592 (6)
H17b	1.4962	0.4548	1.1902	0.119*	0.592 (6)
H18a	1.6368	0.6610	1.1706	0.176*	0.592 (6)
H18b	1.6303	0.5254	1.1287	0.176*	0.592 (6)
H19a	1.7632	0.5952	1.2837	0.212*	0.592 (6)
H19b	1.6881	0.4733	1.2874	0.212*	0.592 (6)
H20a	1.8675	0.4129	1.2784	0.363*	0.592 (6)
H20b	1.8429	0.4885	1.1949	0.363*	0.592 (6)
H20c	1.7684	0.3665	1.1993	0.363*	0.592 (6)
H17c	1.5534	0.6240	1.2257	0.168*	0.413 (5)
H17d	1.4928	0.4892	1.2189	0.168*	0.413 (5)
H18c	1.6349	0.5692	1.1248	0.176*	0.413 (5)
H18d	1.5666	0.4389	1.1090	0.176*	0.413 (5)
H19'	1.7105	0.3459	1.2196	0.212*	0.413 (5)
H20d	1.7973	0.5969	1.2441	0.291*	0.413 (5)
H20e	1.8659	0.4716	1.2907	0.291*	0.413 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.076 (1)	0.045 (1)	0.085 (1)	0.003 (1)	−0.028 (1)	0.002 (1)
O2	0.091 (1)	0.041 (1)	0.089 (1)	−0.009 (1)	−0.022 (1)	−0.003 (1)
O3	0.072 (1)	0.052 (1)	0.099 (1)	0.002 (1)	−0.027 (1)	−0.001 (1)
O4	0.088 (1)	0.054 (1)	0.144 (2)	0.000 (1)	−0.026 (1)	0.019 (1)
N1	0.059 (1)	0.036 (1)	0.061 (1)	0.001 (1)	−0.006 (1)	0.002 (1)
N2	0.075 (1)	0.057 (1)	0.095 (2)	0.006 (1)	−0.020 (1)	0.000 (1)
C1	0.065 (1)	0.042 (1)	0.063 (1)	−0.004 (1)	−0.011 (1)	0.002 (1)
C2	0.059 (1)	0.038 (1)	0.057 (1)	−0.001 (1)	−0.003 (1)	0.000 (1)
C3	0.073 (2)	0.037 (1)	0.075 (2)	0.003 (1)	−0.009 (1)	−0.001 (1)
C4	0.068 (2)	0.047 (1)	0.076 (2)	0.008 (1)	−0.011 (1)	0.005 (1)
C5	0.060 (1)	0.053 (1)	0.063 (1)	0.002 (1)	−0.006 (1)	0.000 (1)
C6	0.062 (1)	0.043 (1)	0.065 (1)	−0.003 (1)	−0.004 (1)	−0.004 (1)
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)
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)
C11	0.063 (2)	0.049 (2)	0.078 (2)	0.002 (1)	−0.001 (1)	0.002 (1)
C12	0.057 (1)	0.055 (2)	0.071 (2)	−0.002 (1)	0.001 (1)	0.001 (1)
C13	0.073 (2)	0.063 (2)	0.111 (2)	−0.012 (1)	−0.005 (2)	0.003 (2)
C14	0.068 (2)	0.096 (3)	0.110 (2)	−0.019 (1)	−0.017 (2)	−0.005 (2)
C15	0.060 (2)	0.096 (2)	0.085 (2)	0.004 (2)	−0.003 (1)	0.010 (2)
C16	0.086 (2)	0.068 (2)	0.110 (2)	0.011 (2)	−0.020 (2)	0.010 (2)
C17	0.085 (9)	0.104 (8)	0.089 (10)	−0.004 (6)	0.001 (6)	0.015 (6)
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)	0.14 (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—C1	1.260 (3)	C4—H4	0.93
O2—C1	1.226 (3)	C6—H6	0.93
O3—C11	1.293 (3)	C7—H7a	0.97
O4—C11	1.201 (3)	C7—H7b	0.97
N1—C6	1.341 (3)	C8—H8a	0.97
N1—C2	1.346 (3)	C8—H8b	0.97
N2—C16	1.326 (3)	C9—H9	0.93
N2—C12	1.332 (3)	C10—H10a	0.93
C1—C2	1.519 (3)	C10—H10b	0.93
C2—C3	1.377 (3)	C7'—H7c	0.97
C3—C4	1.383 (3)	C7'—H7d	0.97
C4—C5	1.390 (3)	C8'—H8c	0.97
C5—C6	1.385 (3)	C8'—H8d	0.97
C5—C7'	1.510 (5)	C9'—H9c	0.97
C5—C7	1.513 (4)	C9'—H9d	0.97
C7—C8	1.498 (4)	C10'—H10c	0.96
C8—C9	1.516 (5)	C10'—H10d	0.96
C9—C10	1.330 (5)	C10'—H10e	0.96
C7'—C8'	1.499 (5)	C13—H13	0.93
C8'—C9'	1.508 (5)	C14—H14	0.93
C9'—C10'	1.477 (5)	C16—H16	0.93
C11—C12	1.503 (3)	C17—H17a	0.97
C12—C13	1.371 (4)	C17—H17b	0.97
C13—C14	1.381 (4)	C18—H18a	0.97
C14—C15	1.374 (4)	C18—H18b	0.97
C15—C16	1.383 (4)	C19—H19a	0.97
C15—C17'	1.508 (5)	C19—H19b	0.97
C15—C17	1.509 (4)	C20—H20a	0.96
C17—C18	1.495 (5)	C20—H20b	0.96
C18—C19	1.502 (5)	C20—H20c	0.96
C19—C20	1.473 (5)	C17'—H17c	0.97
C17'—C18'	1.499 (5)	C17'—H17d	0.97
C18'—C19'	1.504 (5)	C18'—H18c	0.97
C19'—C20'	1.341 (5)	C18'—H18d	0.97
O3—H3o	0.86 (1)	C19'—H19'	0.93
N1—H1n	0.85 (1)	C20'—H20d	0.93
C3—H3	0.93	C20'—H20e	0.93

C6—N1—C2	123.6 (2)	H10a—C10—H10b	120.0
C16—N2—C12	117.2 (2)	C8'—C7'—H7c	109.3
O2—C1—O1	128.1 (2)	C5—C7'—H7c	109.3
O2—C1—C2	117.5 (2)	C8'—C7'—H7d	109.3
O1—C1—C2	114.4 (2)	C5—C7'—H7d	109.3
N1—C2—C3	117.9 (2)	H7c—C7'—H7d	108.0
N1—C2—C1	117.1 (2)	C7'—C8'—H8c	108.6
C3—C2—C1	125.0 (2)	C9'—C8'—H8c	108.6
C2—C3—C4	119.7 (2)	C7'—C8'—H8d	108.6
C3—C4—C5	121.5 (2)	C9'—C8'—H8d	108.6
C6—C5—C4	116.6 (2)	H8c—C8'—H8d	107.6
C6—C5—C7'	120 (3)	C10'—C9'—H9c	105.1
C4—C5—C7'	123 (2)	C8'—C9'—H9c	105.1
C6—C5—C7	121 (2)	C10'—C9'—H9d	105.1
C4—C5—C7	122 (2)	C8'—C9'—H9d	105.1
N1—C6—C5	120.7 (2)	H9c—C9'—H9d	105.9
C8—C7—C5	114.9 (8)	C9'—C10'—H10c	109.5
C7—C8—C9	113.3 (6)	C9'—C10'—H10d	109.5
C10—C9—C8	118.6 (9)	H10c—C10'—H10d	109.5
C8'—C7'—C5	112 (1)	C9'—C10'—H10e	109.5
C7'—C8'—C9'	115 (1)	H10c—C10'—H10e	109.5
C10'—C9'—C8'	129 (1)	H10d—C10'—H10e	109.5
O4—C11—O3	124.2 (2)	C12—C13—H13	120.3
O4—C11—C12	121.4 (2)	C14—C13—H13	120.3
O3—C11—C12	114.4 (2)	C15—C14—H14	119.8
N2—C12—C13	121.8 (2)	C13—C14—H14	119.8
N2—C12—C11	118.5 (2)	N2—C16—H16	117.0
C13—C12—C11	119.6 (2)	C15—C16—H16	117.0
C12—C13—C14	119.5 (3)	C18—C17—H17a	109.0
C15—C14—C13	120.3 (3)	C15—C17—H17a	109.0
C14—C15—C16	115.2 (2)	C18—C17—H17b	109.0
C14—C15—C17'	121 (1)	C15—C17—H17b	109.0
C16—C15—C17'	124 (1)	H17a—C17—H17b	107.8
C14—C15—C17	124.7 (5)	C17—C18—H18a	109.7
C16—C15—C17	120.1 (5)	C19—C18—H18a	109.7
N2—C16—C15	126.1 (3)	C17—C18—H18b	109.7
C18—C17—C15	112.7 (7)	C19—C18—H18b	109.7
C17—C18—C19	110.0 (8)	H18a—C18—H18b	108.2
C20—C19—C18	113 (1)	C20—C19—H19a	109.1
C18'—C17'—C15	113 (1)	C18—C19—H19a	109.1
C17'—C18'—C19'	116 (1)	C20—C19—H19b	109.1
C20'—C19'—C18'	117 (2)	C18—C19—H19b	109.1
C11—O3—H3o	118 (3)	H19a—C19—H19b	107.8
C6—N1—H1n	119 (2)	C19—C20—H20a	109.5
C2—N1—H1n	117 (2)	C19—C20—H20b	109.5
C2—C3—H3	120.1	H20a—C20—H20b	109.5
C4—C3—H3	120.1	C19—C20—H20c	109.5
C3—C4—H4	119.3	H20a—C20—H20c	109.5
C5—C4—H4	119.3	H20b—C20—H20c	109.5
N1—C6—H6	119.7	C18'—C17'—H17c	109.0
C5—C6—H6	119.7	C15—C17'—H17c	109.0
C8—C7—H7a	108.5	C18'—C17'—H17d	109.0
C5—C7—H7a	108.5	C15—C17'—H17d	109.0
C8—C7—H7b	108.5	H17c—C17'—H17d	107.8
C5—C7—H7b	108.5	C17'—C18'—H18c	108.2
H7a—C7—H7b	107.5	C19'—C18'—H18c	108.2
C7—C8—H8a	108.9	C17'—C18'—H18d	108.2
C9—C8—H8a	108.9	C19'—C18'—H18d	108.2
C7—C8—H8b	108.9	H18c—C18'—H18d	107.4
C9—C8—H8b	108.9	C20'—C19'—H19'	121.4
H8a—C8—H8b	107.7	C18'—C19'—H19'	121.4
C10—C9—H9	120.7	C19'—C20'—H20d	120.0
C8—C9—H9	120.7	C19'—C20'—H20e	120.0
C9—C10—H10a	120.0	H20d—C20'—H20e	120.0
C9—C10—H10b	120.0

C6—N1—C2—C3	1.3 (4)	C16—N2—C12—C13	−0.8 (5)
C6—N1—C2—C1	−178.2 (2)	C16—N2—C12—C11	−177.2 (3)
O2—C1—C2—N1	−176.8 (2)	O4—C11—C12—N2	−178.8 (3)
O1—C1—C2—N1	3.4 (3)	O3—C11—C12—N2	2.6 (4)
O2—C1—C2—C3	3.8 (4)	O4—C11—C12—C13	4.8 (4)
O1—C1—C2—C3	−176.0 (2)	O3—C11—C12—C13	−173.8 (3)
N1—C2—C3—C4	−1.6 (4)	N2—C12—C13—C14	1.3 (5)
C1—C2—C3—C4	177.8 (2)	C11—C12—C13—C14	177.6 (3)
C2—C3—C4—C5	0.7 (4)	C12—C13—C14—C15	−0.9 (5)
C3—C4—C5—C6	0.7 (4)	C13—C14—C15—C16	0.1 (5)
C3—C4—C5—C7'	174 (1)	C13—C14—C15—C17'	178 (1)
C3—C4—C5—C7	−174.0 (7)	C13—C14—C15—C17	−177.8 (7)
C2—N1—C6—C5	0.1 (4)	C12—N2—C16—C15	0.0 (5)
C4—C5—C6—N1	−1.1 (4)	C14—C15—C16—N2	0.4 (6)
C7'—C5—C6—N1	−175.1 (9)	C17'—C15—C16—N2	−178 (1)
C7—C5—C6—N1	173.6 (7)	C17—C15—C16—N2	178.4 (7)
C6—C5—C7—C8	99 (3)	C14—C15—C17—C18	−64 (1)
C4—C5—C7—C8	−87 (3)	C16—C15—C17—C18	118.0 (8)
C5—C7—C8—C9	179 (2)	C15—C17—C18—C19	172.5 (9)
C7—C8—C9—C10	−161 (2)	C17—C18—C19—C20	131 (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···A	D—H	H···A	D···A	D—H···A
O3—H3o···O1	0.86 (1)	1.71 (1)	2.557 (2)	168 (4)
N1—H1n···O2ⁱ	0.85 (1)	1.98 (2)	2.703 (2)	141 (2)

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

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