2-Carbamoyl-3-pyridyl benzoate

Gasser, G.; Stoeckli-Evans, H.

doi:10.1107/S1600536807008112

2-Carbamoyl-3-pyridyl benzoate

The title compound, C₁₃H₁₀N₂O₃, crystallizes with two independent molecules (A and B) per asymmetric unit. In both molecules, there is an intramolecular N—H

N hydrogen bond and the two molecules are linked by C—H

π interactions. The main differences between the two molecules concern the orientation of the amide unit with respect to the pyridine ring, and the orientation of the carboxylate group with respect to both the pyridine and phenyl rings. In the crystal structure, symmetry-related molecules are linked by N—H

N, N—H

O and C—H

O hydrogen bonds, forming a slab-like structure, two molecules thick, which are stacked in the c-axis direction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008112/hg2186sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008112/hg2186Isup2.hkl Contains datablock I

CCDC reference: 640363

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.003 Å
R factor = 0.056
wR factor = 0.159
Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         900 Deg.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.19
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        PYB
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        PHA

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-Carbamoyl-3-pyridyl benzoate top

Crystal data top

C₁₃H₁₀N₂O₃	Z = 4
M_r = 242.23	F(000) = 504
Triclinic, P1	D_x = 1.388 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1955 (10) Å	Cell parameters from 98 reflections
b = 10.5805 (13) Å	θ = 10.2–30.6°
c = 14.6556 (15) Å	µ = 0.10 mm⁻¹
α = 104.457 (9)°	T = 153 K
β = 100.951 (9)°	Block, colourless
γ = 102.729 (9)°	0.60 × 0.49 × 0.38 mm
V = 1159.3 (2) Å³

Data collection top

Stoe AED2 four-circle diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 25.1°, θ_min = 1.5°
Graphite monochromator	h = −9→9
2θ/ω scans	k = −12→12
4037 measured reflections	l = 0→17
4037 independent reflections	2 standard reflections every 60 min
3777 reflections with I > 2σ(I)	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.159	w = 1/[σ²(F_o²) + (0.0903P)² + 0.4249P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
4037 reflections	Δρ_max = 0.26 e Å⁻³
342 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.070 (6)

Special details top

Experimental. ¹H-RMN (CDCl₃, 400 MHz): δ=8.50 (dd, 1H, ³J(9,8)=4.52 Hz, ⁴J(9,7)= 1.40 Hz, H⁹), δ=8.25 (dd, 2H, ³J(3,2)=8.10 Hz, ⁴J(3,1)= 1.40 Hz, H³), δ=7.76 (s, b, 1H, H¹³), δ=7.64 (dd, 1H, ³J(7,8)=8.20 Hz, ⁴J(7,9)= 1.40 Hz, H⁹), δ=7.63 (dd, 1H, ³J(1,2)=8.10 Hz, ⁴J(1,3)= 1.40 Hz, H¹), δ=7.57 (dd, 1H, ³J(8,7)=8.20 Hz, ⁴J(8,9)=4.52 Hz, H⁸), δ=7.52 (dd, 2H, ³J(2,1)=³J(2,3)=8.10 Hz, H²), δ=5.76 (s, b, 1H, H¹²). ¹³C-RMN (CDCl₃, 400 MHz): δ=165.36 (1 C, C¹¹), δ=165.18 (1 C, C⁵), δ=147.81 (1 C, C⁶), δ=145.52 (1 C, C⁹), δ=141.37 (1 C, C¹⁰), δ=133.60 (1 C, C¹), δ=133.05 (2 C, C⁸), δ=130.40 (2 C, C³), δ=129.19 (1 C, C⁴), δ=128.51 (1 C, C²), δ=127.59 (1 C, C⁷). ESI MS m/z: 241 ([M—H]^-) IR (KBr disc, cm^-1) 3402(m), 3305(m), 2924(m), 2854(m), 1745(s), 1669(s), 1601(m), 1449(s), 1368(m), 1299(m), 1262(s), 1215(s), 1175(m), 1108(m), 1047(s), 1023(s), 867(w), 794(w), 706(s), 627(m), 484(w). M.p: 130°C. TLC (Dichloromethane:Ether 13:1): Rf = 0.33.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Only one equivalent of data were measured, hence R_int = 0.0.

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

	x	y	z	U_iso*/U_eq
O1	0.3533 (2)	0.42130 (18)	0.15757 (10)	0.0654 (6)
O2	0.27575 (17)	0.57103 (13)	0.26540 (9)	0.0468 (4)
O3	0.0911 (2)	0.32310 (16)	0.27798 (11)	0.0619 (5)
N1	−0.1587 (2)	0.42160 (18)	0.09933 (13)	0.0522 (6)
N2	−0.1102 (3)	0.1944 (2)	0.14011 (15)	0.0630 (7)
C2	−0.0110 (2)	0.43384 (19)	0.16391 (13)	0.0421 (6)
C3	0.1234 (3)	0.55248 (19)	0.19558 (13)	0.0442 (6)
C4	0.1080 (3)	0.6612 (2)	0.16188 (17)	0.0566 (7)
C5	−0.0446 (3)	0.6487 (2)	0.09728 (18)	0.0636 (8)
C6	−0.1721 (3)	0.5282 (2)	0.06773 (17)	0.0611 (8)
C7	0.3796 (3)	0.4935 (2)	0.23966 (14)	0.0452 (6)
C8	0.5227 (2)	0.50676 (19)	0.32300 (14)	0.0449 (6)
C9	0.6262 (3)	0.4201 (2)	0.31003 (18)	0.0576 (7)
C10	0.7558 (3)	0.4253 (3)	0.3880 (2)	0.0690 (9)
C11	0.7818 (3)	0.5169 (3)	0.47842 (18)	0.0639 (8)
C12	0.6814 (3)	0.6047 (2)	0.49161 (16)	0.0584 (7)
C13	0.5505 (3)	0.6000 (2)	0.41394 (14)	0.0504 (6)
C14	−0.0053 (3)	0.3118 (2)	0.19952 (14)	0.0458 (6)
O21	0.6245 (2)	0.77596 (18)	0.24922 (15)	0.0769 (7)
O22	0.71922 (19)	1.00190 (14)	0.27724 (10)	0.0519 (5)
O23	0.77359 (18)	0.89864 (14)	0.09346 (10)	0.0510 (5)
N21	0.3500 (2)	0.92382 (18)	0.06708 (12)	0.0497 (6)
N22	0.5289 (3)	0.7528 (2)	−0.01236 (14)	0.0591 (6)
C22	0.5043 (3)	0.92774 (18)	0.11992 (13)	0.0426 (6)
C23	0.5607 (3)	0.9976 (2)	0.21928 (14)	0.0470 (6)
C24	0.4608 (3)	1.0697 (2)	0.26273 (16)	0.0603 (8)
C25	0.3053 (3)	1.0698 (3)	0.20679 (17)	0.0637 (8)
C26	0.2545 (3)	0.9943 (2)	0.11039 (17)	0.0576 (8)
C27	0.7397 (3)	0.8790 (2)	0.28470 (15)	0.0511 (7)
C28	0.9153 (3)	0.8926 (2)	0.34210 (14)	0.0479 (6)
C29	0.9481 (3)	0.7746 (2)	0.35712 (16)	0.0563 (7)
C30	1.1082 (3)	0.7809 (3)	0.41162 (18)	0.0652 (9)
C31	1.2348 (3)	0.9024 (3)	0.45074 (18)	0.0684 (9)
C32	1.2020 (3)	1.0193 (3)	0.43663 (19)	0.0688 (8)
C33	1.0429 (3)	1.0148 (2)	0.38174 (17)	0.0573 (7)
C34	0.6149 (3)	0.85769 (19)	0.06589 (14)	0.0440 (6)
H2A	−0.126 (3)	0.113 (3)	0.154 (2)	0.076 (8)*
H2B	−0.185 (4)	0.189 (3)	0.091 (2)	0.085 (9)*
H4	0.20050	0.74260	0.18280	0.0680*
H5	−0.06100	0.72210	0.07370	0.0760*
H6	−0.27630	0.51960	0.02210	0.0730*
H9	0.60850	0.35710	0.24770	0.0690*
H10	0.82670	0.36560	0.37920	0.0830*
H11	0.86970	0.51930	0.53190	0.0770*
H12	0.70140	0.66870	0.55380	0.0700*
H13	0.48040	0.66020	0.42300	0.0600*
H22A	0.594 (4)	0.715 (3)	−0.051 (2)	0.076 (8)*
H22B	0.411 (4)	0.728 (3)	−0.031 (2)	0.078 (8)*
H24	0.49840	1.11880	0.33030	0.0720*
H25	0.23520	1.12090	0.23440	0.0760*
H26	0.14550	0.99190	0.07230	0.0690*
H29	0.86050	0.69020	0.32990	0.0680*
H30	1.13080	0.70060	0.42210	0.0780*
H31	1.34530	0.90610	0.48760	0.0820*
H32	1.28960	1.10360	0.46490	0.0830*
H33	1.02140	1.09540	0.37130	0.0690*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0676 (10)	0.0831 (11)	0.0410 (8)	0.0432 (9)	0.0011 (7)	0.0014 (7)
O2	0.0439 (7)	0.0456 (7)	0.0419 (7)	0.0197 (6)	−0.0044 (6)	0.0033 (5)
O3	0.0683 (10)	0.0614 (9)	0.0464 (8)	0.0177 (8)	−0.0133 (7)	0.0216 (7)
N1	0.0495 (10)	0.0566 (10)	0.0477 (9)	0.0230 (8)	−0.0047 (7)	0.0168 (8)
N2	0.0665 (13)	0.0460 (10)	0.0601 (12)	0.0097 (9)	−0.0171 (10)	0.0182 (9)
C2	0.0438 (10)	0.0461 (10)	0.0354 (9)	0.0216 (8)	−0.0003 (7)	0.0106 (7)
C3	0.0463 (11)	0.0461 (10)	0.0380 (9)	0.0226 (8)	0.0009 (8)	0.0082 (8)
C4	0.0624 (13)	0.0465 (11)	0.0606 (13)	0.0226 (10)	0.0048 (10)	0.0176 (10)
C5	0.0734 (15)	0.0591 (13)	0.0679 (14)	0.0365 (12)	0.0069 (12)	0.0292 (11)
C6	0.0614 (14)	0.0679 (14)	0.0577 (13)	0.0331 (11)	−0.0030 (10)	0.0262 (11)
C7	0.0440 (10)	0.0473 (10)	0.0424 (10)	0.0190 (8)	0.0040 (8)	0.0106 (8)
C8	0.0393 (10)	0.0461 (10)	0.0468 (11)	0.0117 (8)	0.0020 (8)	0.0169 (8)
C9	0.0506 (12)	0.0583 (12)	0.0607 (13)	0.0238 (10)	0.0015 (10)	0.0150 (10)
C10	0.0536 (13)	0.0712 (15)	0.0819 (17)	0.0291 (12)	−0.0015 (12)	0.0269 (13)
C11	0.0487 (12)	0.0722 (15)	0.0644 (14)	0.0127 (11)	−0.0084 (10)	0.0307 (12)
C12	0.0555 (13)	0.0630 (13)	0.0465 (11)	0.0093 (10)	−0.0039 (9)	0.0184 (10)
C13	0.0488 (11)	0.0529 (11)	0.0447 (11)	0.0149 (9)	0.0009 (9)	0.0146 (9)
C14	0.0443 (10)	0.0501 (11)	0.0415 (10)	0.0187 (8)	−0.0003 (8)	0.0153 (8)
O21	0.0613 (10)	0.0649 (11)	0.0973 (13)	0.0050 (8)	−0.0119 (9)	0.0475 (10)
O22	0.0573 (9)	0.0509 (8)	0.0420 (7)	0.0227 (6)	−0.0047 (6)	0.0115 (6)
O23	0.0462 (8)	0.0509 (8)	0.0547 (8)	0.0215 (6)	0.0032 (6)	0.0148 (6)
N21	0.0494 (10)	0.0560 (10)	0.0456 (9)	0.0266 (8)	0.0018 (7)	0.0163 (7)
N22	0.0522 (11)	0.0605 (11)	0.0526 (11)	0.0239 (9)	0.0020 (9)	−0.0019 (8)
C22	0.0476 (10)	0.0412 (9)	0.0402 (10)	0.0194 (8)	0.0042 (8)	0.0140 (8)
C23	0.0517 (11)	0.0481 (10)	0.0424 (10)	0.0219 (9)	0.0033 (8)	0.0156 (8)
C24	0.0739 (15)	0.0659 (13)	0.0448 (11)	0.0350 (12)	0.0116 (10)	0.0130 (10)
C25	0.0744 (16)	0.0743 (15)	0.0587 (13)	0.0473 (13)	0.0211 (11)	0.0228 (11)
C26	0.0554 (13)	0.0691 (14)	0.0581 (13)	0.0365 (11)	0.0087 (10)	0.0244 (11)
C27	0.0553 (12)	0.0553 (12)	0.0471 (11)	0.0180 (10)	0.0061 (9)	0.0263 (9)
C28	0.0539 (12)	0.0576 (12)	0.0371 (9)	0.0223 (9)	0.0081 (8)	0.0199 (8)
C29	0.0619 (13)	0.0592 (12)	0.0531 (12)	0.0244 (10)	0.0088 (10)	0.0243 (10)
C30	0.0699 (15)	0.0771 (16)	0.0654 (14)	0.0398 (13)	0.0154 (12)	0.0359 (12)
C31	0.0584 (14)	0.0890 (18)	0.0602 (14)	0.0313 (13)	0.0030 (11)	0.0271 (13)
C32	0.0588 (14)	0.0717 (15)	0.0678 (15)	0.0179 (12)	0.0000 (11)	0.0201 (12)
C33	0.0576 (13)	0.0589 (13)	0.0550 (12)	0.0208 (10)	0.0049 (10)	0.0202 (10)
C34	0.0468 (11)	0.0444 (10)	0.0421 (10)	0.0212 (8)	0.0031 (8)	0.0147 (8)

Geometric parameters (Å, º) top

O1—C7	1.203 (2)	C12—C13	1.391 (3)
O2—C3	1.397 (3)	C4—H4	0.9500
O2—C7	1.347 (3)	C5—H5	0.9500
O3—C14	1.227 (3)	C6—H6	0.9500
O21—C27	1.195 (3)	C9—H9	0.9500
O22—C23	1.395 (3)	C10—H10	0.9500
O22—C27	1.375 (3)	C11—H11	0.9500
O23—C34	1.228 (3)	C12—H12	0.9500
N1—C6	1.340 (3)	C13—H13	0.9500
N1—C2	1.346 (2)	C22—C34	1.508 (3)
N2—C14	1.321 (3)	C22—C23	1.392 (3)
N2—H2A	0.92 (3)	C23—C24	1.374 (3)
N2—H2B	0.83 (3)	C24—C25	1.379 (4)
N21—C22	1.338 (3)	C25—C26	1.369 (3)
N21—C26	1.335 (3)	C27—C28	1.479 (3)
N22—C34	1.325 (3)	C28—C33	1.379 (3)
N22—H22A	0.93 (3)	C28—C29	1.394 (3)
N22—H22B	0.91 (3)	C29—C30	1.379 (4)
C2—C14	1.515 (3)	C30—C31	1.370 (4)
C2—C3	1.382 (3)	C31—C32	1.378 (4)
C3—C4	1.381 (3)	C32—C33	1.380 (4)
C4—C5	1.376 (4)	C24—H24	0.9500
C5—C6	1.368 (3)	C25—H25	0.9500
C7—C8	1.478 (3)	C26—H26	0.9500
C8—C9	1.383 (3)	C29—H29	0.9500
C8—C13	1.389 (3)	C30—H30	0.9500
C9—C10	1.385 (4)	C31—H31	0.9500
C10—C11	1.379 (4)	C32—H32	0.9500
C11—C12	1.373 (4)	C33—H33	0.9500

O1···O3	3.191 (2)	C22···O21	2.941 (3)
O1···C2	3.035 (2)	C24···C9^x	3.494 (3)
O1···C14	3.147 (3)	C26···C34^ix	3.550 (3)
O1···N22ⁱ	2.909 (3)	C27···C34	3.110 (3)
O2···C30ⁱⁱ	3.390 (3)	C27···O23	2.922 (3)
O2···O3	2.794 (2)	C28···C32^xi	3.518 (3)
O3···O1	3.191 (2)	C29···C4^iv	3.427 (3)
O3···C12ⁱⁱⁱ	3.340 (3)	C30···O2^iv	3.390 (3)
O3···C7	2.879 (3)	C30···C4^iv	3.561 (3)
O3···C11ⁱⁱⁱ	3.390 (3)	C30···C3^iv	3.513 (3)
O3···O2	2.794 (2)	C32···C28^xi	3.518 (3)
O21···C22	2.941 (3)	C34···C26^ix	3.550 (3)
O21···C34	3.014 (3)	C34···N21^ix	3.376 (3)
O21···O23	3.198 (2)	C34···C27	3.110 (3)
O21···C8	3.288 (3)	C34···O21	3.014 (3)
O21···C7	3.166 (3)	C6···H22B^vi	2.83 (3)
O22···O23	2.801 (2)	C8···H29	2.9800
O23···C27	2.922 (3)	C9···H29	2.9800
O23···C5^iv	3.316 (3)	C10···H11^xii	2.9400
O23···O21	3.198 (2)	C11···H11^xii	2.9900
O23···O22	2.801 (2)	C12···H32^xi	2.9400
O23···N2^v	2.922 (3)	C13···H29	3.1000
O1···H9	2.5700	C13···H32^xi	3.0400
O1···H22Aⁱ	2.03 (3)	C22···H2A^v	3.10 (3)
O1···H6^vi	2.8400	C23···H2A^v	3.02 (3)
O2···H13	2.4000	C24···H9^x	3.0900
O3···H10ⁱⁱ	2.9000	C26···H2B^vi	2.97 (3)
O3···H25^vii	2.6600	C26···H4	3.0800
O3···H11ⁱⁱⁱ	2.7800	C34···H2A^v	2.86 (3)
O3···H12ⁱⁱⁱ	2.6900	H2A···C34^viii	2.86 (3)
O21···H29	2.5300	H2A···O23^viii	2.12 (3)
O22···H2A^v	2.74 (3)	H2A···C22^viii	3.10 (3)
O22···H33	2.4400	H2A···O22^viii	2.74 (3)
O23···H5^iv	2.5300	H2A···C23^viii	3.02 (3)
O23···H2A^v	2.12 (3)	H2B···H22B^vi	2.34 (5)
N1···N22^vi	3.021 (3)	H2B···N21^vi	2.31 (3)
N1···N2	2.710 (3)	H2B···C26^vi	2.97 (3)
N2···O23^viii	2.922 (3)	H2B···N1	2.39 (3)
N2···N1	2.710 (3)	H4···C26	3.0800
N2···N21^vi	3.066 (3)	H5···O23ⁱⁱ	2.5300
N21···C34^ix	3.376 (3)	H6···O1^vi	2.8400
N21···N22	2.747 (3)	H9···O1	2.5700
N21···N2^vi	3.066 (3)	H9···C24^vii	3.0900
N22···O1ⁱ	2.909 (3)	H10···H11^xii	2.4500
N22···N21	2.747 (3)	H10···O3^iv	2.9000
N22···N1^vi	3.021 (3)	H11···O3ⁱⁱⁱ	2.7800
N1···H22B^vi	2.18 (3)	H11···H10^xii	2.4500
N1···H2B	2.39 (3)	H11···C10^xii	2.9400
N21···H22B	2.42 (3)	H11···C11^xii	2.9900
N21···H2B^vi	2.31 (3)	H11···H11^xii	2.5600
C2···O1	3.035 (2)	H11···H30^xii	2.5800
C3···C30ⁱⁱ	3.513 (3)	H12···H32^xi	2.4800
C4···C29ⁱⁱ	3.427 (3)	H12···O3ⁱⁱⁱ	2.6900
C4···C30ⁱⁱ	3.561 (3)	H13···O2	2.4000
C5···O23ⁱⁱ	3.316 (3)	H22A···O1ⁱ	2.03 (3)
C7···O3	2.879 (3)	H22B···N21	2.42 (3)
C7···C14	3.171 (3)	H22B···N1^vi	2.18 (3)
C7···O21	3.166 (3)	H22B···C6^vi	2.83 (3)
C8···O21	3.288 (3)	H22B···H2B^vi	2.34 (5)
C9···C24^vii	3.494 (3)	H25···O3^x	2.6600
C11···C13ⁱⁱⁱ	3.544 (4)	H29···O21	2.5300
C11···O3ⁱⁱⁱ	3.390 (3)	H29···C8	2.9800
C12···C13ⁱⁱⁱ	3.302 (3)	H29···C9	2.9800
C12···C12ⁱⁱⁱ	3.385 (3)	H29···C13	3.1000
C12···O3ⁱⁱⁱ	3.340 (3)	H30···H11^xii	2.5800
C13···C12ⁱⁱⁱ	3.302 (3)	H32···C12^xi	2.9400
C13···C11ⁱⁱⁱ	3.544 (4)	H32···C13^xi	3.0400
C14···C7	3.171 (3)	H32···H12^xi	2.4800
C14···O1	3.147 (3)	H33···O22	2.4400

C3—O2—C7	117.08 (15)	C10—C11—H11	120.00
C23—O22—C27	116.05 (17)	C11—C12—H12	120.00
C2—N1—C6	118.05 (19)	C13—C12—H12	120.00
H2A—N2—H2B	112 (3)	C12—C13—H13	120.00
C14—N2—H2B	123 (2)	C8—C13—H13	120.00
C14—N2—H2A	124.7 (17)	N21—C22—C23	120.9 (2)
C22—N21—C26	118.65 (18)	N21—C22—C34	116.78 (16)
H22A—N22—H22B	122 (3)	C23—C22—C34	122.3 (2)
C34—N22—H22B	120.4 (19)	O22—C23—C24	117.73 (18)
C34—N22—H22A	116.8 (19)	O22—C23—C22	122.7 (2)
N1—C2—C3	120.80 (19)	C22—C23—C24	119.6 (2)
N1—C2—C14	115.75 (18)	C23—C24—C25	119.0 (2)
C3—C2—C14	123.45 (17)	C24—C25—C26	118.3 (2)
C2—C3—C4	120.5 (2)	N21—C26—C25	123.4 (2)
O2—C3—C2	122.46 (18)	O22—C27—C28	112.11 (18)
O2—C3—C4	117.01 (19)	O21—C27—C28	125.9 (2)
C3—C4—C5	118.3 (2)	O21—C27—O22	122.0 (2)
C4—C5—C6	118.5 (2)	C27—C28—C29	116.8 (2)
N1—C6—C5	123.8 (2)	C27—C28—C33	123.3 (2)
O2—C7—C8	112.37 (16)	C29—C28—C33	119.9 (2)
O1—C7—C8	125.5 (2)	C28—C29—C30	119.7 (2)
O1—C7—O2	122.1 (2)	C29—C30—C31	120.3 (3)
C7—C8—C9	118.53 (19)	C30—C31—C32	120.1 (2)
C7—C8—C13	121.54 (18)	C31—C32—C33	120.5 (3)
C9—C8—C13	119.88 (19)	C28—C33—C32	119.6 (2)
C8—C9—C10	119.9 (2)	O23—C34—N22	123.7 (2)
C9—C10—C11	120.1 (3)	O23—C34—C22	120.88 (18)
C10—C11—C12	120.4 (2)	N22—C34—C22	115.4 (2)
C11—C12—C13	120.0 (2)	C23—C24—H24	120.00
C8—C13—C12	119.7 (2)	C25—C24—H24	120.00
O3—C14—C2	121.55 (19)	C24—C25—H25	121.00
O3—C14—N2	123.3 (2)	C26—C25—H25	121.00
N2—C14—C2	115.19 (18)	N21—C26—H26	118.00
C3—C4—H4	121.00	C25—C26—H26	118.00
C5—C4—H4	121.00	C28—C29—H29	120.00
C6—C5—H5	121.00	C30—C29—H29	120.00
C4—C5—H5	121.00	C29—C30—H30	120.00
C5—C6—H6	118.00	C31—C30—H30	120.00
N1—C6—H6	118.00	C30—C31—H31	120.00
C10—C9—H9	120.00	C32—C31—H31	120.00
C8—C9—H9	120.00	C31—C32—H32	120.00
C11—C10—H10	120.00	C33—C32—H32	120.00
C9—C10—H10	120.00	C28—C33—H33	120.00
C12—C11—H11	120.00	C32—C33—H33	120.00

C7—O2—C3—C2	67.2 (3)	C13—C8—C9—C10	0.8 (3)
C7—O2—C3—C4	−115.7 (2)	C7—C8—C13—C12	176.9 (2)
C3—O2—C7—O1	7.5 (3)	C9—C8—C13—C12	−0.6 (3)
C3—O2—C7—C8	−171.54 (17)	C8—C9—C10—C11	−0.1 (4)
C23—O22—C27—C28	176.25 (17)	C9—C10—C11—C12	−0.9 (4)
C23—O22—C27—O21	−5.0 (3)	C10—C11—C12—C13	1.1 (4)
C27—O22—C23—C22	−62.2 (3)	C11—C12—C13—C8	−0.4 (4)
C27—O22—C23—C24	120.1 (2)	N21—C22—C23—O22	178.75 (19)
C6—N1—C2—C14	178.13 (19)	N21—C22—C23—C24	−3.6 (3)
C2—N1—C6—C5	0.0 (3)	C34—C22—C23—O22	−3.6 (3)
C6—N1—C2—C3	−0.8 (3)	C34—C22—C23—C24	174.2 (2)
C22—N21—C26—C25	−0.7 (3)	N21—C22—C34—O23	149.7 (2)
C26—N21—C22—C34	−174.34 (19)	N21—C22—C34—N22	−29.2 (3)
C26—N21—C22—C23	3.5 (3)	C23—C22—C34—O23	−28.1 (3)
N1—C2—C3—C4	0.4 (3)	C23—C22—C34—N22	153.0 (2)
N1—C2—C3—O2	177.37 (18)	O22—C23—C24—C25	178.6 (2)
C14—C2—C3—O2	−1.5 (3)	C22—C23—C24—C25	0.8 (3)
C14—C2—C3—C4	−178.4 (2)	C23—C24—C25—C26	1.9 (4)
N1—C2—C14—O3	−156.0 (2)	C24—C25—C26—N21	−2.0 (4)
N1—C2—C14—N2	24.2 (3)	O21—C27—C28—C29	−0.9 (3)
C3—C2—C14—O3	22.9 (3)	O21—C27—C28—C33	−179.7 (2)
C3—C2—C14—N2	−156.9 (2)	O22—C27—C28—C29	177.80 (19)
O2—C3—C4—C5	−176.3 (2)	O22—C27—C28—C33	−0.9 (3)
C2—C3—C4—C5	0.8 (3)	C27—C28—C29—C30	−178.8 (2)
C3—C4—C5—C6	−1.5 (4)	C33—C28—C29—C30	0.0 (3)
C4—C5—C6—N1	1.2 (4)	C27—C28—C33—C32	178.3 (2)
O2—C7—C8—C13	−5.7 (3)	C29—C28—C33—C32	−0.4 (3)
O1—C7—C8—C9	−7.1 (3)	C28—C29—C30—C31	−0.1 (4)
O1—C7—C8—C13	175.3 (2)	C29—C30—C31—C32	0.7 (4)
O2—C7—C8—C9	171.84 (19)	C30—C31—C32—C33	−1.1 (4)
C7—C8—C9—C10	−176.7 (2)	C31—C32—C33—C28	1.0 (4)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z; (v) x+1, y+1, z; (vi) −x, −y+1, −z; (vii) x, y−1, z; (viii) x−1, y−1, z; (ix) −x+1, −y+2, −z; (x) x, y+1, z; (xi) −x+2, −y+2, −z+1; (xii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1	0.83 (3)	2.39 (3)	2.710 (3)	103 (2)
N22—H22B···N21	0.91 (3)	2.42 (3)	2.747 (3)	101 (2)
C4—H4···Py(B)	0.95	2.95	3.831 (2)	155
C29—H29···Ph(A)	0.95	2.78	3.533 (3)	136
N2—H2A···O23^viii	0.92 (3)	2.12 (3)	2.922 (3)	145 (2)
N2—H2B···N21^vi	0.83 (3)	2.31 (3)	3.066 (3)	151 (3)
N22—H22A···O1ⁱ	0.93 (3)	2.03 (3)	2.909 (3)	158 (3)
N22—H22B···N1^vi	0.91 (3)	2.18 (3)	3.021 (3)	153 (3)
C5—H5···O23ⁱⁱ	0.95	2.53	3.316 (3)	140

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (vi) −x, −y+1, −z; (viii) x−1, y−1, z.

Dihedral angles (°) between various best least-squares planes in molecules A & B top

Plane-plane	Molecule A	Molecule B
py-Ph	63.35 (8)	63.45 (8)
py-amide	23.82(129	29.29(109
py-carboxylate	69.27 (8)	62.57 (9)
Ph-carboxylate	7.33(159	1.79(129

Planes in molecules A & B, respectively: py = [N1,C2-C6], [N21,C22-C26]; Ph = [C8-C13 ], [C28-C33]; amide = [C2,C14,N2,O3], [C22,C34,N22,O23]; carboxylate = [C8,C7,O1,O2], [C28,C27,O21,O22].

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