Direct observation of various reaction pathways of arylnitrenes in different crystal environments caused by acid–base complex formation

Mitsumori, T.; Sekine, A.; Uekusa, H.; Ohashi, Y.

doi:10.1107/S010876811003661X

Direct observation of various reaction pathways of arylnitrenes in different crystal environments caused by acid–base complex formation

T. Mitsumori, A. Sekine, H. Uekusa and Y. Ohashi

The structures of reaction intermediates, arylnitrenes and their final products have been successfully analyzed by X-rays using acid–base complex formation. The acid–base complexes of 2-azidobenzoic acid (2a), 3-azidobenzoic acid (3a) and 4-azidobenzoic acid (4a) were made with dibenzylamine (db), N-benzyl-2-phenylethylamine (bp) and dicyclohexylamine (dc). For the complex crystals of (3a) and db (3a-db), and (4a) and db (4a-db) two forms of (I) and (II) were obtained. Eight types of complex crystals, (2a-db), (3a-db-I), (3a-db-II), (3a-dc), (4a-db-I), (4a-db-II), (4a-bp) and (4a-dc), suitable for X-ray analysis were obtained. When the crystals were irradiated with UV light at low temperatures, the reactions proceeded keeping the single-crystal form in the five crystals (2a-db), (3a-db-I), (3a-db-II), (3a-dc) and (4a-bp). Less than 25% of each azidobenzoic acids was transformed into an arylnitrene and dinitrogen. In three crystals the arylnitrenes produced gave new final products; 2,1-benzisoxazolone was observed for (2a-db) and trans-azobenzenes (i.e. dimerized nitrenes) were obtained for (3a-db-II) and (4a-bp). For (3a-db-I) and (3a-dc) the intermediate arylnitrenes were observed but did not transform to new products. All the structural changes were directly observed by X-ray analysis because the incomplete reactions occurred with retention crystallinity. The crystal environment, including the hydrogen bonding between the benzoic acid and the amine, places restrictions on the movement of the arylnitrene and influences the reaction pathway followed for conversion of the arylnitrene to its final product.

Keywords: arylnitrene; reaction pathway; acid–base complex formation; crystalline state reaction; X-ray analysis.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S010876811003661X/og5043sup1.cif Contains datablocks 2a-db-i, 3a-db-I-i, 3a-db-II-i, 3a-dc-i, 4a-bp-i, 2a-db-f, 3a-db-I-f, 3a-db-II-f, 3a-dc-f, 4a-bp-f, 4a-db-I-i, 4a-db-II-i, 4a-dc-i, global
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50432a-db-isup2.fcf Contains datablock 2a-db-i
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50433a-db-I-isup3.fcf Contains datablock 3a-db-I-i
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50433a-db-II-isup4.fcf Contains datablock 3a-db-II-i
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50433a-dc-isup5.fcf Contains datablock 3a-dc-i
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50434a-bp-isup6.fcf Contains datablock 4a-bp-i
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50432a-db-fsup7.fcf Contains datablock 2a-db-f
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50433a-db-I-fsup8.fcf Contains datablock 3a-db-I-f
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50433a-db-II-fsup9.fcf Contains datablock 3a-db-II-f
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50433a-dc-fsup10.fcf Contains datablock 3a-dc-f
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50434a-bp-fsup11.fcf Contains datablock 4a-bp-f
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50434a-db-I-isup12.fcf Contains datablock 4a-db-I-i
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50434a-db-II-isup13.fcf Contains datablock 4a-db-II-i
	Structure factor file (CIF format) https://doi.org/10.1107/S010876811003661X/og50434a-dc-isup14.fcf Contains datablock 4a-dc-i

CCDC references: 810870; 810871; 810872; 810873; 810874; 810875; 810876; 810877; 810878; 810879; 810880; 810881; 810882

Computing details top

Data collection: Siemens SMART for 2a-db-i, 3a-db-I-i, 3a-db-II-i, 3a-dc-i, 4a-bp-i, 2a-db-f, 3a-db-I-f, 3a-db-II-f, 3a-dc-f, 4a-bp-f, 4a-db-I-i, 4a-dc-i; PROCESS-AUTO (Rigaku, 1998) for 4a-db-II-i. Cell refinement: Siemens SMART for 2a-db-i, 3a-db-I-i, 3a-db-II-i, 3a-dc-i, 4a-bp-i, 2a-db-f, 3a-db-I-f, 3a-db-II-f, 3a-dc-f, 4a-bp-f, 4a-db-I-i, 4a-dc-i; PROCESS-AUTO (Rigaku, 1998) for 4a-db-II-i. Data reduction: SHELXS97 (Sheldrick, 1990) for 2a-db-i; Siemens SAINT & SADABS for 3a-db-I-i, 3a-dc-i, 4a-bp-i, 2a-db-f, 3a-db-I-f, 3a-db-II-f, 3a-dc-f, 4a-bp-f, 4a-db-I-i, 4a-dc-i; TEXSAN (Rigaku, 1999) for 4a-db-II-i. For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Window (Farrugia,1998) for 2a-db-i, 3a-db-I-i, 3a-dc-i, 4a-bp-i, 2a-db-f, 3a-db-I-f, 3a-db-II-f, 3a-dc-f, 4a-bp-f, 4a-db-I-i, 4a-dc-i; Siemens SAINT & SADABS for 3a-db-II-i; ORTEP-3 for Windows (Farrugia, 1998) for 4a-db-II-i. Software used to prepare material for publication: SHELXTL97 for 2a-db-i, 3a-db-I-i, 3a-db-II-i, 3a-dc-i, 4a-bp-i, 2a-db-f, 3a-db-I-f, 3a-db-II-f, 3a-dc-f, 4a-bp-f, 4a-db-I-i, 4a-dc-i; SHELXL97 (Sheldrick, 1997) for 4a-db-II-i.

Dibenzylammonium 2-azidebenzoate (2a-db-i) top

Crystal data top

C₂₁H₂₀N₄O₂	F(000) = 760
M_r = 360.41	D_x = 1.250 Mg m⁻³
Monoclinic, Cc	Melting point: not measured K
a = 19.9575 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0329 (3) Å	Cell parameters from 6026 reflections
c = 9.9849 (3) Å	µ = 0.08 mm⁻¹
β = 106.640 (2)°	T = 88 K
V = 1915.57 (11) Å³	Block, pale-yellow
Z = 4	0.41 × 0.34 × 0.22 mm

Data collection top

Bruker SMART CCD area detector system diffractometer	2788 independent reflections
Radiation source: rotating anode	2668 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 30.0°, θ_min = 2.3°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −28→28
T_min = 0.967, T_max = 0.982	k = −14→14
14815 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Only H-atom coordinates refined
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0531P)²] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
2788 reflections	Δρ_max = 0.21 e Å⁻³
306 parameters	Δρ_min = −0.17 e Å⁻³
2 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C7	0.52584 (6)	0.28417 (11)	0.17755 (12)	0.0156 (2)
C1	0.51110 (6)	0.07384 (11)	0.31620 (12)	0.0157 (2)
C2	0.53558 (7)	−0.05101 (12)	0.37278 (12)	0.0186 (2)
H2	0.5110 (11)	−0.1016 (19)	0.427 (2)	0.022*
C3	0.59777 (7)	−0.10205 (13)	0.35731 (13)	0.0210 (2)
H3	0.6127 (11)	−0.190 (2)	0.393 (2)	0.025*
C4	0.63557 (7)	−0.03052 (13)	0.28332 (13)	0.0215 (2)
H4	0.6789 (11)	−0.065 (2)	0.269 (2)	0.026*
C5	0.60980 (7)	0.09231 (13)	0.22353 (12)	0.0187 (2)
H5	0.6341 (10)	0.1426 (19)	0.173 (2)	0.022*
C6	0.54779 (6)	0.14702 (11)	0.23929 (11)	0.0152 (2)
N1	0.44752 (6)	0.12966 (11)	0.33350 (12)	0.0211 (2)
N2	0.42178 (6)	0.06875 (12)	0.41564 (12)	0.0229 (2)
N3	0.39299 (7)	0.02463 (15)	0.48862 (15)	0.0350 (3)
O1	0.49980 (5)	0.36640 (9)	0.24439 (9)	0.02026 (18)
O2	0.53708 (5)	0.30844 (9)	0.06113 (9)	0.02034 (18)
C8	0.41548 (6)	0.43306 (12)	0.49418 (13)	0.0188 (2)
H81	0.4107 (10)	0.4689 (19)	0.583 (2)	0.023*
H82	0.4000 (10)	0.341 (2)	0.487 (2)	0.023*
C9	0.37123 (6)	0.51203 (12)	0.37163 (13)	0.0199 (2)
C10	0.32648 (7)	0.44712 (13)	0.25664 (14)	0.0225 (2)
H10	0.3267 (11)	0.345 (2)	0.257 (2)	0.027*
C11	0.28343 (7)	0.52001 (16)	0.14560 (15)	0.0270 (3)
H11	0.2533 (12)	0.476 (2)	0.065 (2)	0.032*
C12	0.28549 (8)	0.65867 (17)	0.14707 (18)	0.0313 (3)
H12	0.2539 (12)	0.709 (2)	0.073 (2)	0.038*
C13	0.33064 (10)	0.72386 (17)	0.2590 (2)	0.0421 (4)
H13	0.3304 (14)	0.826 (3)	0.269 (3)	0.051*
C14	0.37258 (9)	0.65203 (15)	0.3726 (2)	0.0369 (4)
H14	0.4055 (14)	0.704 (2)	0.456 (3)	0.044*
C15	0.53440 (6)	0.35001 (12)	0.61997 (13)	0.0177 (2)
H151	0.5217 (10)	0.262 (2)	0.599 (2)	0.021*
H152	0.5219 (10)	0.3775 (18)	0.703 (2)	0.021*
C16	0.61182 (6)	0.36816 (11)	0.63853 (12)	0.0173 (2)
C17	0.64423 (7)	0.30495 (13)	0.54862 (13)	0.0210 (2)
H17	0.6159 (10)	0.242 (2)	0.477 (2)	0.025*
C18	0.71519 (7)	0.32473 (14)	0.56244 (14)	0.0230 (2)
H18	0.7358 (11)	0.283 (2)	0.496 (2)	0.028*
C19	0.75472 (7)	0.40689 (15)	0.66909 (17)	0.0284 (3)
H19	0.8021 (13)	0.424 (2)	0.682 (2)	0.034*
C20	0.72335 (8)	0.46672 (18)	0.76160 (19)	0.0355 (3)
H20	0.7524 (13)	0.520 (2)	0.838 (3)	0.043*
C21	0.65199 (7)	0.44864 (15)	0.74643 (16)	0.0271 (3)
H21	0.6302 (12)	0.496 (2)	0.804 (2)	0.032*
N4	0.49197 (5)	0.43544 (10)	0.50181 (11)	0.01514 (18)
H01	0.5073 (9)	0.5185 (19)	0.5221 (19)	0.018 (4)*
H02	0.4977 (9)	0.4062 (18)	0.420 (2)	0.016 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.0182 (5)	0.0134 (5)	0.0149 (5)	0.0007 (4)	0.0040 (4)	−0.0002 (4)
C1	0.0172 (5)	0.0146 (5)	0.0147 (5)	−0.0003 (4)	0.0038 (4)	−0.0009 (4)
C2	0.0233 (6)	0.0154 (5)	0.0161 (5)	−0.0007 (4)	0.0042 (4)	0.0017 (4)
C3	0.0270 (6)	0.0171 (5)	0.0168 (5)	0.0044 (4)	0.0027 (4)	0.0008 (4)
C4	0.0240 (6)	0.0220 (6)	0.0187 (5)	0.0074 (4)	0.0065 (4)	−0.0002 (4)
C5	0.0213 (5)	0.0205 (5)	0.0152 (5)	0.0025 (4)	0.0065 (4)	−0.0008 (4)
C6	0.0182 (5)	0.0134 (5)	0.0136 (5)	0.0004 (4)	0.0041 (4)	−0.0002 (4)
N1	0.0192 (5)	0.0207 (5)	0.0254 (5)	0.0010 (4)	0.0099 (4)	0.0043 (4)
N2	0.0193 (5)	0.0243 (5)	0.0253 (5)	−0.0010 (4)	0.0065 (4)	0.0013 (4)
N3	0.0275 (6)	0.0435 (8)	0.0387 (7)	−0.0020 (5)	0.0168 (5)	0.0104 (6)
O1	0.0295 (5)	0.0165 (4)	0.0172 (4)	0.0046 (3)	0.0104 (3)	0.0007 (3)
O2	0.0308 (5)	0.0163 (4)	0.0167 (4)	0.0028 (3)	0.0111 (3)	0.0016 (3)
C8	0.0164 (5)	0.0216 (5)	0.0196 (6)	−0.0003 (4)	0.0069 (4)	−0.0015 (4)
C9	0.0153 (5)	0.0206 (5)	0.0237 (6)	0.0032 (4)	0.0056 (4)	−0.0025 (4)
C10	0.0207 (5)	0.0249 (6)	0.0219 (6)	−0.0032 (5)	0.0060 (4)	0.0005 (5)
C11	0.0200 (6)	0.0366 (7)	0.0233 (6)	−0.0022 (5)	0.0044 (5)	0.0026 (6)
C12	0.0201 (6)	0.0363 (7)	0.0357 (7)	0.0071 (5)	0.0052 (5)	0.0078 (6)
C13	0.0377 (8)	0.0241 (7)	0.0539 (11)	0.0104 (6)	−0.0039 (7)	−0.0001 (7)
C14	0.0327 (8)	0.0208 (6)	0.0454 (9)	0.0058 (6)	−0.0077 (7)	−0.0070 (6)
C15	0.0175 (5)	0.0175 (5)	0.0171 (5)	−0.0011 (4)	0.0032 (4)	0.0021 (4)
C16	0.0173 (5)	0.0146 (5)	0.0183 (5)	−0.0001 (4)	0.0027 (4)	0.0013 (4)
C17	0.0217 (6)	0.0231 (6)	0.0175 (5)	−0.0007 (4)	0.0044 (4)	−0.0007 (4)
C18	0.0219 (6)	0.0259 (6)	0.0215 (6)	0.0034 (4)	0.0069 (5)	0.0035 (5)
C19	0.0172 (6)	0.0291 (7)	0.0372 (8)	−0.0003 (5)	0.0050 (5)	−0.0021 (6)
C20	0.0214 (6)	0.0366 (8)	0.0449 (9)	−0.0044 (5)	0.0037 (6)	−0.0185 (7)
C21	0.0210 (6)	0.0277 (6)	0.0304 (7)	−0.0009 (5)	0.0040 (5)	−0.0125 (5)
N4	0.0150 (4)	0.0153 (4)	0.0153 (4)	0.0005 (3)	0.0045 (3)	−0.0011 (3)

Geometric parameters (Å, º) top

C7—O1	1.2628 (14)	C10—H10	1.03 (2)
C7—O2	1.2689 (14)	C11—C12	1.392 (2)
C7—C6	1.5201 (16)	C11—H11	0.96 (2)
C1—C2	1.4031 (16)	C12—C13	1.383 (3)
C1—C6	1.4096 (15)	C12—H12	0.97 (2)
C1—N1	1.4420 (15)	C13—C14	1.401 (2)
C2—C3	1.3915 (18)	C13—H13	1.03 (3)
C2—H2	0.97 (2)	C14—H14	1.04 (3)
C3—C4	1.3962 (19)	C15—N4	1.5072 (15)
C3—H3	0.96 (2)	C15—C16	1.5136 (17)
C4—C5	1.4013 (17)	C15—H151	0.93 (2)
C4—H4	0.98 (2)	C15—H152	0.969 (19)
C5—C6	1.4032 (16)	C16—C17	1.3997 (17)
C5—H5	0.94 (2)	C16—C21	1.4003 (17)
N1—N2	1.2455 (15)	C17—C18	1.3972 (18)
N1—O1	2.8379 (14)	C17—H17	1.00 (2)
N1—O2	4.0733 (14)	C18—C19	1.398 (2)
N1—N1ⁱ	5.6297 (10)	C18—H18	0.97 (2)
N2—N3	1.1389 (17)	C19—C20	1.392 (2)
C8—N4	1.5067 (15)	C19—H19	0.93 (2)
C8—C9	1.5120 (18)	C20—C21	1.400 (2)
C8—H81	0.986 (19)	C20—H20	0.97 (3)
C8—H82	0.97 (2)	C21—H21	0.94 (2)
C9—C10	1.3974 (17)	N4—H01	0.891 (19)
C9—C14	1.4048 (19)	N4—H02	0.906 (19)
C10—C11	1.3988 (19)

O1—C7—O2	124.48 (11)	C9—C10—H10	117.5 (12)
O1—C7—C6	119.44 (10)	C11—C10—H10	121.8 (12)
O2—C7—C6	116.06 (10)	C12—C11—C10	120.30 (14)
C2—C1—C6	120.60 (11)	C12—C11—H11	118.4 (13)
C2—C1—N1	121.02 (10)	C10—C11—H11	121.3 (13)
C6—C1—N1	118.37 (10)	C13—C12—C11	119.46 (14)
C3—C2—C1	120.17 (11)	C13—C12—H12	120.0 (14)
C3—C2—H2	118.6 (12)	C11—C12—H12	120.4 (14)
C1—C2—H2	121.2 (12)	C12—C13—C14	120.73 (15)
C2—C3—C4	120.26 (11)	C12—C13—H13	121.9 (16)
C2—C3—H3	118.9 (12)	C14—C13—H13	116.9 (16)
C4—C3—H3	120.8 (12)	C13—C14—C9	120.21 (14)
C3—C4—C5	119.30 (11)	C13—C14—H14	119.0 (14)
C3—C4—H4	122.2 (12)	C9—C14—H14	120.8 (14)
C5—C4—H4	118.4 (12)	N4—C15—C16	110.63 (9)
C4—C5—C6	121.61 (11)	N4—C15—H151	108.2 (12)
C4—C5—H5	121.2 (12)	C16—C15—H151	110.3 (12)
C6—C5—H5	117.2 (12)	N4—C15—H152	106.3 (11)
C5—C6—C1	118.02 (10)	C16—C15—H152	111.4 (12)
C5—C6—C7	118.01 (10)	H151—C15—H152	110.0 (16)
C1—C6—C7	123.93 (10)	C17—C16—C21	119.13 (11)
N2—N1—C1	115.55 (10)	C17—C16—C15	120.67 (11)
N2—N1—O1	151.06 (9)	C21—C16—C15	120.20 (11)
C1—N1—O1	82.67 (6)	C18—C17—C16	120.92 (12)
N2—N1—O2	176.63 (9)	C18—C17—H17	120.7 (11)
C1—N1—O2	61.42 (6)	C16—C17—H17	118.3 (11)
O1—N1—O2	31.91 (2)	C17—C18—C19	119.59 (12)
N2—N1—N1ⁱ	23.73 (7)	C17—C18—H18	119.0 (12)
C1—N1—N1ⁱ	98.64 (7)	C19—C18—H18	121.4 (12)
O1—N1—N1ⁱ	139.31 (4)	C20—C19—C18	119.80 (13)
O2—N1—N1ⁱ	155.10 (2)	C20—C19—H19	117.5 (14)
N3—N2—N1	172.25 (15)	C18—C19—H19	122.7 (14)
C7—O1—N1	82.11 (7)	C19—C20—C21	120.62 (13)
C7—O2—N1	22.69 (6)	C19—C20—H20	118.5 (15)
N4—C8—C9	112.41 (10)	C21—C20—H20	120.9 (15)
N4—C8—H81	107.9 (11)	C20—C21—C16	119.90 (13)
C9—C8—H81	110.6 (11)	C20—C21—H21	120.1 (14)
N4—C8—H82	108.4 (11)	C16—C21—H21	119.9 (14)
C9—C8—H82	110.0 (11)	C8—N4—C15	111.38 (9)
H81—C8—H82	107.4 (16)	C8—N4—H01	107.6 (12)
C10—C9—C14	118.55 (12)	C15—N4—H01	106.0 (12)
C10—C9—C8	120.57 (11)	C8—N4—H02	109.7 (11)
C14—C9—C8	120.86 (12)	C15—N4—H02	109.5 (12)
C9—C10—C11	120.70 (12)	H01—N4—H02	112.7 (16)

C6—C1—C2—C3	2.09 (18)	O2—N1—O1—C7	−14.31 (6)
N1—C1—C2—C3	−178.75 (11)	N1ⁱ—N1—O1—C7	125.53 (7)
C1—C2—C3—C4	−1.13 (19)	O1—C7—O2—N1	−114.4 (2)
C2—C3—C4—C5	−0.75 (19)	C6—C7—O2—N1	67.33 (14)
C3—C4—C5—C6	1.72 (19)	N2—N1—O2—C7	−113.9 (16)
C4—C5—C6—C1	−0.78 (18)	C1—N1—O2—C7	−87.69 (17)
C4—C5—C6—C7	176.74 (11)	O1—N1—O2—C7	39.18 (15)
C2—C1—C6—C5	−1.13 (16)	N1ⁱ—N1—O2—C7	−47.79 (17)
N1—C1—C6—C5	179.69 (11)	N4—C8—C9—C10	108.68 (13)
C2—C1—C6—C7	−178.49 (11)	N4—C8—C9—C14	−73.22 (16)
N1—C1—C6—C7	2.33 (16)	C14—C9—C10—C11	−0.7 (2)
O1—C7—C6—C5	−140.53 (12)	C8—C9—C10—C11	177.45 (12)
O2—C7—C6—C5	37.78 (16)	C9—C10—C11—C12	1.1 (2)
O1—C7—C6—C1	36.82 (17)	C10—C11—C12—C13	0.2 (2)
O2—C7—C6—C1	−144.86 (11)	C11—C12—C13—C14	−2.0 (3)
C2—C1—N1—N2	8.94 (17)	C12—C13—C14—C9	2.4 (3)
C6—C1—N1—N2	−171.88 (11)	C10—C9—C14—C13	−1.1 (3)
C2—C1—N1—O1	165.35 (11)	C8—C9—C14—C13	−179.21 (17)
C6—C1—N1—O1	−15.47 (10)	N4—C15—C16—C17	−78.18 (14)
C2—C1—N1—O2	−169.41 (12)	N4—C15—C16—C21	101.89 (14)
C6—C1—N1—O2	9.76 (8)	C21—C16—C17—C18	−2.14 (19)
C2—C1—N1—N1ⁱ	26.44 (11)	C15—C16—C17—C18	177.93 (12)
C6—C1—N1—N1ⁱ	−154.38 (9)	C16—C17—C18—C19	1.2 (2)
C1—N1—N2—N3	173.7 (11)	C17—C18—C19—C20	0.9 (2)
O1—N1—N2—N3	48.8 (12)	C18—C19—C20—C21	−1.9 (3)
O2—N1—N2—N3	−160.9 (11)	C19—C20—C21—C16	0.9 (3)
N1ⁱ—N1—N2—N3	126.0 (12)	C17—C16—C21—C20	1.1 (2)
O2—C7—O1—N1	149.41 (12)	C15—C16—C21—C20	−178.97 (14)
C6—C7—O1—N1	−32.42 (10)	C9—C8—N4—C15	−176.89 (10)
N2—N1—O1—C7	162.54 (19)	C16—C15—N4—C8	−172.32 (9)
C1—N1—O1—C7	30.79 (9)

Symmetry code: (i) x, −y, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H01···O2ⁱⁱ	0.891 (19)	1.841 (19)	2.7311 (13)	178.7 (19)
N4—H01···O1ⁱⁱ	0.891 (19)	2.544 (18)	3.1027 (14)	121.4 (14)
N4—H02···O1	0.906 (19)	1.810 (19)	2.7094 (13)	171.5 (17)
N4—H02···N1	0.906 (19)	2.991 (18)	3.4885 (15)	116.3 (13)

Symmetry code: (ii) x, −y+1, z+1/2.

Dibenzylammonium 3-azidebenzoate (3a-db-I-i) top

Crystal data top

C₂₁H₂₀N₄O₂	D_x = 1.245 Mg m⁻³
M_r = 360.41	Melting point: not measured K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.9705 (1) Å	Cell parameters from 8192 reflections
b = 14.4208 (1) Å	µ = 0.08 mm⁻¹
c = 14.8689 (2) Å	T = 80 K
V = 1923.47 (4) Å³	Needle, pale-yellow
Z = 4	0.40 × 0.20 × 0.15 mm
F(000) = 760

Data collection top

Bruker SMART CCD area detector system diffractometer	3163 independent reflections
Radiation source: rotating anode	2908 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −12→12
T_min = 0.968, T_max = 0.988	k = −20→20
30731 measured reflections	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Only H-atom coordinates refined
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0542P)² + 0.0162P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max < 0.001
3163 reflections	Δρ_max = 0.25 e Å⁻³
324 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
C7	0.42563 (13)	0.23810 (8)	0.14946 (7)	0.0175 (2)
C1	0.32640 (14)	0.31922 (8)	0.38437 (8)	0.0214 (2)
C2	0.31631 (14)	0.29550 (8)	0.29364 (7)	0.0187 (2)
H2	0.2235 (18)	0.3030 (10)	0.2611 (10)	0.018 (4)*
C3	0.44015 (12)	0.25957 (7)	0.24902 (7)	0.0168 (2)
C4	0.57361 (13)	0.24659 (8)	0.29573 (8)	0.0201 (2)
H4	0.6589 (19)	0.2247 (12)	0.2638 (11)	0.022 (4)*
C5	0.58356 (15)	0.27224 (9)	0.38620 (8)	0.0239 (2)
H5	0.674 (2)	0.2635 (13)	0.4176 (11)	0.030 (4)*
C6	0.46016 (16)	0.30905 (9)	0.43072 (8)	0.0250 (2)
H6	0.470 (2)	0.3279 (14)	0.4913 (12)	0.038 (5)*
N1	0.20195 (14)	0.35639 (9)	0.43364 (7)	0.0293 (2)
N2	0.08173 (14)	0.35293 (9)	0.39244 (8)	0.0308 (3)
N3	−0.03312 (15)	0.35272 (12)	0.36100 (10)	0.0438 (3)
O1	0.29982 (9)	0.25381 (7)	0.11410 (6)	0.02326 (18)
O2	0.53704 (10)	0.20693 (7)	0.10808 (6)	0.02380 (19)
C8	0.41324 (14)	0.36028 (8)	−0.07267 (8)	0.0206 (2)
H81	0.363 (2)	0.4012 (13)	−0.0309 (12)	0.028 (4)*
H82	0.517 (2)	0.3485 (12)	−0.0540 (11)	0.027 (4)*
C9	0.40358 (13)	0.39821 (8)	−0.16715 (8)	0.0179 (2)
C10	0.51563 (14)	0.37881 (8)	−0.22938 (8)	0.0217 (2)
H10	0.607 (2)	0.3453 (13)	−0.2109 (11)	0.028 (4)*
C11	0.50239 (16)	0.40879 (10)	−0.31829 (9)	0.0277 (3)
H11	0.581 (2)	0.3955 (14)	−0.3619 (14)	0.045 (5)*
C12	0.37921 (17)	0.46022 (10)	−0.34463 (9)	0.0305 (3)
H12	0.366 (2)	0.4806 (14)	−0.4094 (12)	0.035 (5)*
C13	0.26903 (16)	0.48192 (9)	−0.28259 (11)	0.0296 (3)
H13	0.190 (2)	0.5175 (15)	−0.3003 (14)	0.046 (6)*
C14	0.28009 (14)	0.45043 (8)	−0.19401 (9)	0.0235 (2)
H14	0.199 (2)	0.4637 (12)	−0.1515 (12)	0.034 (5)*
C15	0.40318 (13)	0.19003 (8)	−0.11058 (8)	0.0190 (2)
H151	0.502 (2)	0.1840 (12)	−0.0880 (11)	0.028 (4)*
H152	0.412 (2)	0.2090 (14)	−0.1757 (13)	0.035 (5)*
C16	0.31125 (13)	0.10347 (8)	−0.09704 (8)	0.0200 (2)
C17	0.31433 (15)	0.05780 (8)	−0.01422 (9)	0.0236 (2)
H17	0.377 (2)	0.0794 (13)	0.0359 (12)	0.032 (5)*
C18	0.22703 (18)	−0.02091 (9)	−0.00042 (10)	0.0317 (3)
H18	0.236 (2)	−0.0557 (14)	0.0594 (14)	0.044 (5)*
C19	0.13615 (17)	−0.05418 (10)	−0.06924 (13)	0.0354 (3)
H19	0.074 (3)	−0.1077 (17)	−0.0620 (14)	0.055 (6)*
C20	0.13448 (16)	−0.00994 (10)	−0.15191 (13)	0.0344 (3)
H20	0.080 (3)	−0.0337 (18)	−0.2019 (15)	0.057 (6)*
C21	0.22123 (15)	0.06936 (9)	−0.16595 (10)	0.0265 (3)
H21	0.227 (2)	0.0995 (13)	−0.2226 (12)	0.032 (4)*
N4	0.33057 (11)	0.27002 (7)	−0.06358 (6)	0.01650 (18)
H02	0.235 (2)	0.2771 (14)	−0.0873 (12)	0.032 (4)*
H01	0.324 (2)	0.2539 (15)	0.0004 (14)	0.035 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.0179 (5)	0.0196 (5)	0.0148 (4)	−0.0012 (4)	0.0013 (4)	−0.0004 (4)
C1	0.0272 (6)	0.0201 (5)	0.0170 (5)	−0.0025 (4)	0.0030 (5)	−0.0005 (4)
C2	0.0203 (5)	0.0198 (5)	0.0160 (5)	−0.0013 (4)	0.0008 (4)	0.0004 (4)
C3	0.0189 (5)	0.0164 (5)	0.0152 (4)	−0.0027 (4)	0.0005 (4)	0.0011 (4)
C4	0.0202 (5)	0.0191 (5)	0.0210 (5)	−0.0021 (4)	−0.0024 (4)	0.0036 (4)
C5	0.0265 (6)	0.0240 (5)	0.0212 (5)	−0.0049 (5)	−0.0070 (5)	0.0043 (4)
C6	0.0352 (7)	0.0247 (6)	0.0150 (5)	−0.0059 (5)	−0.0035 (5)	0.0005 (4)
N1	0.0336 (6)	0.0353 (6)	0.0190 (5)	0.0024 (5)	0.0065 (4)	−0.0041 (4)
N2	0.0323 (6)	0.0349 (6)	0.0252 (5)	0.0006 (5)	0.0120 (5)	−0.0080 (5)
N3	0.0283 (6)	0.0607 (9)	0.0425 (7)	0.0043 (6)	0.0101 (6)	−0.0192 (7)
O1	0.0179 (4)	0.0355 (5)	0.0164 (3)	0.0033 (4)	0.0000 (3)	−0.0014 (3)
O2	0.0171 (4)	0.0321 (5)	0.0222 (4)	0.0018 (3)	0.0024 (3)	−0.0055 (4)
C8	0.0242 (5)	0.0185 (5)	0.0191 (5)	−0.0068 (4)	−0.0016 (4)	−0.0020 (4)
C9	0.0190 (5)	0.0141 (4)	0.0204 (5)	−0.0035 (4)	0.0004 (4)	−0.0007 (4)
C10	0.0203 (5)	0.0209 (5)	0.0240 (5)	−0.0028 (4)	0.0024 (4)	0.0008 (4)
C11	0.0297 (7)	0.0301 (6)	0.0234 (6)	−0.0072 (5)	0.0040 (5)	0.0020 (5)
C12	0.0362 (7)	0.0294 (6)	0.0259 (6)	−0.0112 (6)	−0.0071 (5)	0.0087 (5)
C13	0.0263 (6)	0.0224 (6)	0.0401 (7)	−0.0035 (5)	−0.0085 (6)	0.0083 (5)
C14	0.0205 (5)	0.0178 (5)	0.0323 (6)	−0.0002 (4)	0.0006 (5)	0.0004 (5)
C15	0.0183 (5)	0.0178 (5)	0.0211 (5)	−0.0006 (4)	0.0034 (4)	−0.0001 (4)
C16	0.0175 (5)	0.0168 (5)	0.0256 (5)	0.0002 (4)	0.0022 (4)	0.0001 (4)
C17	0.0267 (6)	0.0188 (5)	0.0253 (6)	0.0004 (5)	0.0054 (5)	0.0012 (4)
C18	0.0366 (7)	0.0205 (6)	0.0381 (7)	−0.0016 (5)	0.0143 (6)	0.0048 (5)
C19	0.0272 (6)	0.0194 (6)	0.0595 (10)	−0.0053 (5)	0.0104 (7)	−0.0008 (6)
C20	0.0237 (6)	0.0236 (6)	0.0560 (10)	−0.0021 (5)	−0.0086 (6)	−0.0047 (6)
C21	0.0246 (6)	0.0201 (5)	0.0350 (7)	0.0009 (5)	−0.0072 (5)	0.0008 (5)
N4	0.0162 (4)	0.0173 (4)	0.0160 (4)	−0.0018 (3)	0.0005 (3)	−0.0007 (3)

Geometric parameters (Å, º) top

C7—O2	1.2568 (14)	C11—C12	1.387 (2)
C7—O1	1.2654 (14)	C11—H11	0.97 (2)
C7—C3	1.5180 (15)	C12—C13	1.388 (2)
C1—C6	1.3915 (18)	C12—H12	1.014 (18)
C1—C2	1.3947 (16)	C13—C14	1.397 (2)
C1—N1	1.4389 (16)	C13—H13	0.92 (2)
C2—C3	1.3938 (16)	C14—H14	0.985 (19)
C2—H2	0.968 (16)	C15—N4	1.4977 (15)
C3—C4	1.3967 (16)	C15—C16	1.5095 (16)
C4—C5	1.3980 (17)	C15—H151	0.954 (18)
C4—H4	0.955 (17)	C15—H152	1.010 (19)
C5—C6	1.395 (2)	C16—C21	1.3943 (17)
C5—H5	0.943 (18)	C16—C17	1.3967 (17)
C6—H6	0.944 (18)	C17—C18	1.3942 (18)
N1—N2	1.2413 (18)	C17—H17	0.981 (19)
N1—N1ⁱ	5.7816 (16)	C18—C19	1.393 (2)
N2—N3	1.1313 (19)	C18—H18	1.02 (2)
C8—N4	1.5041 (15)	C19—C20	1.385 (3)
C8—C9	1.5100 (16)	C19—H19	0.96 (2)
C8—H81	0.966 (19)	C20—C21	1.3990 (19)
C8—H82	0.986 (18)	C20—H20	0.95 (2)
C9—C10	1.3944 (16)	C21—H21	0.949 (19)
C9—C14	1.3978 (17)	N4—H02	0.94 (2)
C10—C11	1.3961 (18)	N4—H01	0.98 (2)
C10—H10	0.989 (18)

O2—C7—O1	124.74 (10)	C13—C12—C11	120.02 (12)
O2—C7—C3	118.83 (10)	C13—C12—H12	118.8 (11)
O1—C7—C3	116.44 (10)	C11—C12—H12	121.1 (11)
C6—C1—C2	120.61 (11)	C12—C13—C14	120.19 (12)
C6—C1—N1	117.14 (11)	C12—C13—H13	119.2 (13)
C2—C1—N1	122.24 (12)	C14—C13—H13	120.6 (13)
C1—C2—C3	119.99 (11)	C13—C14—C9	120.05 (12)
C1—C2—H2	120.7 (9)	C13—C14—H14	119.3 (11)
C3—C2—H2	119.3 (9)	C9—C14—H14	120.6 (11)
C2—C3—C4	119.76 (10)	N4—C15—C16	109.70 (9)
C2—C3—C7	118.13 (10)	N4—C15—H151	108.1 (10)
C4—C3—C7	122.09 (10)	C16—C15—H151	112.8 (10)
C5—C4—C3	119.85 (11)	N4—C15—H152	105.8 (11)
C5—C4—H4	121.0 (10)	C16—C15—H152	113.2 (11)
C3—C4—H4	118.9 (10)	H151—C15—H152	106.9 (15)
C6—C5—C4	120.44 (11)	C21—C16—C17	119.54 (11)
C6—C5—H5	119.8 (10)	C21—C16—C15	120.67 (11)
C4—C5—H5	119.7 (11)	C17—C16—C15	119.79 (11)
C1—C6—C5	119.31 (11)	C18—C17—C16	120.17 (13)
C1—C6—H6	121.3 (12)	C18—C17—H17	117.8 (11)
C5—C6—H6	119.4 (12)	C16—C17—H17	122.1 (11)
N2—N1—C1	114.07 (10)	C19—C18—C17	120.05 (13)
N2—N1—N1ⁱ	145.20 (10)	C19—C18—H18	121.0 (12)
C1—N1—N1ⁱ	51.26 (6)	C17—C18—H18	118.8 (12)
N3—N2—N1	174.39 (13)	C20—C19—C18	119.97 (13)
N4—C8—C9	111.64 (9)	C20—C19—H19	117.6 (13)
N4—C8—H81	104.1 (11)	C18—C19—H19	122.4 (13)
C9—C8—H81	110.5 (10)	C19—C20—C21	120.19 (14)
N4—C8—H82	106.9 (10)	C19—C20—H20	122.2 (14)
C9—C8—H82	112.3 (10)	C21—C20—H20	117.5 (14)
H81—C8—H82	111.1 (14)	C16—C21—C20	120.06 (13)
C10—C9—C14	119.33 (11)	C16—C21—H21	117.3 (11)
C10—C9—C8	120.22 (11)	C20—C21—H21	122.5 (11)
C14—C9—C8	120.42 (11)	C15—N4—C8	114.22 (9)
C11—C10—C9	120.32 (11)	C15—N4—H02	107.9 (12)
C11—C10—H10	119.0 (10)	C8—N4—H02	109.0 (12)
C9—C10—H10	120.6 (10)	C15—N4—H01	107.1 (13)
C12—C11—C10	120.04 (13)	C8—N4—H01	108.7 (12)
C12—C11—H11	119.4 (12)	H02—N4—H01	109.8 (16)
C10—C11—H11	120.6 (12)

C6—C1—C2—C3	1.25 (17)	N4—C8—C9—C14	83.88 (13)
N1—C1—C2—C3	−179.88 (11)	C14—C9—C10—C11	−1.98 (17)
C1—C2—C3—C4	0.64 (17)	C8—C9—C10—C11	175.91 (11)
C1—C2—C3—C7	−177.77 (10)	C9—C10—C11—C12	1.68 (19)
O2—C7—C3—C2	178.98 (11)	C10—C11—C12—C13	0.0 (2)
O1—C7—C3—C2	−0.69 (15)	C11—C12—C13—C14	−1.4 (2)
O2—C7—C3—C4	0.61 (16)	C12—C13—C14—C9	1.08 (19)
O1—C7—C3—C4	−179.06 (11)	C10—C9—C14—C13	0.60 (17)
C2—C3—C4—C5	−1.88 (16)	C8—C9—C14—C13	−177.28 (11)
C7—C3—C4—C5	176.46 (10)	N4—C15—C16—C21	103.63 (13)
C3—C4—C5—C6	1.27 (17)	N4—C15—C16—C17	−75.32 (13)
C2—C1—C6—C5	−1.86 (18)	C21—C16—C17—C18	−0.51 (18)
N1—C1—C6—C5	179.21 (11)	C15—C16—C17—C18	178.45 (11)
C4—C5—C6—C1	0.60 (18)	C16—C17—C18—C19	−0.1 (2)
C6—C1—N1—N2	−171.38 (12)	C17—C18—C19—C20	1.1 (2)
C2—C1—N1—N2	9.72 (18)	C18—C19—C20—C21	−1.5 (2)
C6—C1—N1—N1ⁱ	−28.76 (8)	C17—C16—C21—C20	0.15 (19)
C2—C1—N1—N1ⁱ	152.34 (14)	C15—C16—C21—C20	−178.80 (12)
C1—N1—N2—N3	177 (100)	C19—C20—C21—C16	0.8 (2)
N1ⁱ—N1—N2—N3	121.1 (17)	C16—C15—N4—C8	179.97 (9)
N4—C8—C9—C10	−93.99 (13)	C9—C8—N4—C15	70.61 (13)

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

Dibenzylammonium 3-azidebenzoate (3a-db-II-i) top

Crystal data top

C₂₁H₂₀N₄O₂	F(000) = 760
M_r = 360.41	D_x = 1.247 Mg m⁻³
Monoclinic, P2₁/c	Melting point: not measured K
a = 10.854 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6662 (17) Å	Cell parameters from 8192 reflections
c = 21.081 (4) Å	µ = 0.08 mm⁻¹
β = 104.51 (3)°	T = 78 K
V = 1919.7 (7) Å³	Needle, pale-yellow
Z = 4	0.31 × 0.16 × 0.12 mm

Data collection top

Bruker SMART CCD area detector system diffractometer	5594 independent reflections
Radiation source: rotating anode	4774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 30.0°, θ_min = 2.4°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −15→15
T_min = 0.975, T_max = 0.990	k = −12→12
29789 measured reflections	l = −29→29

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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F²) = 0.100	Only H-atom coordinates refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0556P)² + 0.3146P] where P = (F_o² + 2F_c²)/3
5594 reflections	(Δ/σ)_max < 0.001
306 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.13691 (6)	0.29862 (7)	0.23145 (3)	0.02011 (13)
O2	0.05607 (6)	0.07489 (7)	0.18594 (3)	0.01954 (13)
C7	0.11946 (7)	0.19795 (9)	0.18647 (4)	0.01607 (15)
C1	0.19693 (8)	0.15944 (9)	0.02087 (4)	0.01656 (15)
C2	0.14119 (7)	0.13516 (9)	0.07295 (4)	0.01573 (15)
H2	0.0761 (11)	0.0573 (13)	0.0689 (5)	0.019*
C3	0.17939 (7)	0.22481 (9)	0.12962 (4)	0.01475 (15)
C4	0.27203 (8)	0.33943 (10)	0.13348 (4)	0.01831 (16)
H4	0.3020 (11)	0.4009 (14)	0.1746 (6)	0.022*
C5	0.32574 (8)	0.36395 (10)	0.08067 (4)	0.02064 (17)
H5	0.3886 (12)	0.4462 (14)	0.0823 (6)	0.025*
C6	0.28934 (8)	0.27418 (10)	0.02406 (4)	0.01921 (16)
H6	0.3244 (11)	0.2939 (14)	−0.0144 (6)	0.023*
N1	0.15087 (8)	0.06217 (10)	−0.03525 (4)	0.02365 (16)
N2	0.21442 (8)	0.06132 (9)	−0.07687 (4)	0.02236 (16)
N3	0.26382 (10)	0.04952 (10)	−0.11808 (4)	0.0319 (2)
N4	0.07443 (6)	0.60347 (8)	0.22062 (3)	0.01476 (13)
H02	0.0140 (13)	0.5934 (16)	0.2484 (7)	0.034 (3)*
H01	0.1099 (12)	0.5039 (16)	0.2201 (6)	0.029 (3)*
C8	0.17221 (8)	0.71933 (9)	0.25497 (4)	0.01651 (15)
H81	0.1961 (11)	0.6876 (13)	0.3021 (6)	0.020*
H82	0.1264 (11)	0.8196 (13)	0.2521 (6)	0.020*
C9	0.28765 (7)	0.72816 (9)	0.22725 (4)	0.01593 (15)
C10	0.28730 (8)	0.82469 (10)	0.17384 (4)	0.01951 (16)
H10	0.2121 (12)	0.8863 (14)	0.1550 (6)	0.023*
C11	0.39423 (9)	0.83345 (11)	0.14836 (5)	0.02432 (18)
H11	0.3920 (12)	0.9021 (15)	0.1109 (6)	0.029*
C12	0.50239 (9)	0.74719 (11)	0.17641 (5)	0.02566 (19)
H12	0.5786 (13)	0.7542 (15)	0.1588 (6)	0.031*
C13	0.50395 (8)	0.65141 (11)	0.22987 (5)	0.02480 (19)
H13	0.5787 (12)	0.5906 (15)	0.2500 (6)	0.030*
C14	0.39680 (8)	0.64185 (10)	0.25522 (4)	0.02007 (16)
H14	0.3991 (11)	0.5761 (14)	0.2921 (6)	0.024*
C15	0.00825 (8)	0.65060 (10)	0.15210 (4)	0.01913 (16)
H151	0.0736 (11)	0.6551 (14)	0.1268 (6)	0.023*
H152	−0.0206 (11)	0.7577 (14)	0.1550 (6)	0.023*
C16	−0.09915 (8)	0.54205 (10)	0.12129 (4)	0.01807 (16)
C17	−0.08819 (9)	0.44219 (11)	0.07093 (4)	0.02378 (18)
H17	−0.0088 (12)	0.4401 (15)	0.0566 (6)	0.029*
C18	−0.18851 (11)	0.34402 (11)	0.04172 (5)	0.0301 (2)
H18	−0.1810 (13)	0.2767 (16)	0.0070 (7)	0.036*
C19	−0.30012 (10)	0.34510 (12)	0.06284 (5)	0.0309 (2)
H19	−0.3695 (13)	0.2758 (17)	0.0425 (7)	0.037*
C20	−0.31160 (9)	0.44408 (12)	0.11325 (5)	0.02638 (19)
H20	−0.3885 (13)	0.4447 (15)	0.1297 (6)	0.032*
C21	−0.21176 (8)	0.54264 (11)	0.14244 (4)	0.02069 (17)
H21	−0.2185 (11)	0.6080 (15)	0.1786 (6)	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0276 (3)	0.0162 (3)	0.0176 (3)	0.0018 (2)	0.0077 (2)	−0.0014 (2)
O2	0.0230 (3)	0.0166 (3)	0.0223 (3)	−0.0014 (2)	0.0118 (2)	−0.0007 (2)
C7	0.0172 (3)	0.0153 (3)	0.0166 (3)	0.0037 (3)	0.0057 (3)	0.0015 (3)
C1	0.0174 (3)	0.0173 (4)	0.0150 (3)	−0.0007 (3)	0.0041 (3)	0.0007 (3)
C2	0.0158 (3)	0.0150 (3)	0.0170 (3)	−0.0007 (3)	0.0053 (3)	0.0010 (3)
C3	0.0148 (3)	0.0142 (3)	0.0156 (3)	0.0018 (3)	0.0044 (3)	0.0015 (3)
C4	0.0177 (4)	0.0183 (4)	0.0180 (4)	−0.0018 (3)	0.0029 (3)	−0.0005 (3)
C5	0.0176 (4)	0.0225 (4)	0.0215 (4)	−0.0057 (3)	0.0042 (3)	0.0013 (3)
C6	0.0179 (4)	0.0225 (4)	0.0178 (4)	−0.0027 (3)	0.0056 (3)	0.0038 (3)
N1	0.0284 (4)	0.0274 (4)	0.0179 (3)	−0.0087 (3)	0.0108 (3)	−0.0054 (3)
N2	0.0299 (4)	0.0198 (3)	0.0191 (3)	−0.0027 (3)	0.0094 (3)	−0.0009 (3)
N3	0.0457 (5)	0.0285 (4)	0.0279 (4)	−0.0059 (4)	0.0210 (4)	−0.0045 (3)
N4	0.0154 (3)	0.0140 (3)	0.0155 (3)	−0.0007 (2)	0.0050 (2)	0.0007 (2)
C8	0.0178 (3)	0.0155 (3)	0.0169 (3)	−0.0027 (3)	0.0055 (3)	−0.0023 (3)
C9	0.0160 (3)	0.0138 (3)	0.0184 (3)	−0.0022 (3)	0.0051 (3)	−0.0024 (3)
C10	0.0193 (4)	0.0166 (4)	0.0239 (4)	−0.0003 (3)	0.0077 (3)	0.0018 (3)
C11	0.0251 (4)	0.0222 (4)	0.0292 (4)	−0.0034 (3)	0.0135 (4)	0.0029 (3)
C12	0.0196 (4)	0.0254 (4)	0.0354 (5)	−0.0033 (3)	0.0131 (4)	−0.0025 (4)
C13	0.0158 (4)	0.0259 (4)	0.0321 (5)	0.0007 (3)	0.0047 (3)	−0.0013 (4)
C14	0.0181 (4)	0.0199 (4)	0.0212 (4)	−0.0008 (3)	0.0031 (3)	0.0005 (3)
C15	0.0181 (4)	0.0209 (4)	0.0176 (4)	−0.0019 (3)	0.0031 (3)	0.0043 (3)
C16	0.0170 (4)	0.0181 (4)	0.0174 (4)	0.0007 (3)	0.0013 (3)	0.0030 (3)
C17	0.0249 (4)	0.0231 (4)	0.0216 (4)	0.0068 (3)	0.0025 (3)	0.0011 (3)
C18	0.0380 (5)	0.0203 (4)	0.0262 (5)	0.0048 (4)	−0.0030 (4)	−0.0035 (4)
C19	0.0300 (5)	0.0222 (4)	0.0321 (5)	−0.0057 (4)	−0.0079 (4)	0.0033 (4)
C20	0.0193 (4)	0.0282 (5)	0.0284 (4)	−0.0040 (3)	−0.0001 (3)	0.0078 (4)
C21	0.0176 (4)	0.0230 (4)	0.0204 (4)	0.0000 (3)	0.0027 (3)	0.0031 (3)

Geometric parameters (Å, º) top

O1—C7	1.2672 (10)	C9—C10	1.4019 (12)
O2—C7	1.2677 (10)	C10—C11	1.3979 (12)
C7—C3	1.5180 (11)	C10—H10	0.973 (12)
C1—C2	1.3959 (11)	C11—C12	1.3925 (14)
C1—C6	1.4020 (11)	C11—H11	0.985 (13)
C1—N1	1.4367 (11)	C12—C13	1.3963 (14)
C2—C3	1.3980 (11)	C12—H12	0.990 (13)
C2—H2	0.965 (11)	C13—C14	1.3988 (13)
C3—C4	1.4012 (11)	C13—H13	0.971 (13)
C4—C5	1.3964 (12)	C14—H14	0.960 (12)
C4—H4	1.000 (12)	C15—C16	1.5120 (12)
C5—C6	1.3962 (12)	C15—H151	0.989 (12)
C5—H5	0.981 (12)	C15—H152	0.987 (12)
C6—H6	0.993 (12)	C16—C17	1.3978 (12)
N1—N2	1.2444 (11)	C16—C21	1.4021 (12)
N2—N3	1.1342 (11)	C17—C18	1.3974 (14)
N4—C15	1.4998 (11)	C17—H17	0.982 (13)
N4—C8	1.5079 (11)	C18—C19	1.3915 (17)
N4—H02	0.986 (13)	C18—H18	0.956 (14)
N4—H01	0.946 (14)	C19—C20	1.3955 (16)
C8—C9	1.5113 (12)	C19—H19	0.975 (14)
C8—H81	1.001 (11)	C20—C21	1.3959 (13)
C8—H82	0.995 (12)	C20—H20	0.980 (13)
C9—C14	1.4002 (12)	C21—H21	0.968 (13)

O1—C7—O2	124.39 (8)	C11—C10—C9	120.38 (8)
O1—C7—C3	118.16 (7)	C11—C10—H10	120.4 (7)
O2—C7—C3	117.45 (7)	C9—C10—H10	119.2 (7)
C2—C1—C6	121.01 (8)	C12—C11—C10	120.04 (8)
C2—C1—N1	115.42 (7)	C12—C11—H11	120.9 (7)
C6—C1—N1	123.55 (8)	C10—C11—H11	119.1 (7)
C1—C2—C3	119.61 (7)	C11—C12—C13	120.02 (8)
C1—C2—H2	119.1 (7)	C11—C12—H12	120.2 (8)
C3—C2—H2	121.3 (7)	C13—C12—H12	119.8 (8)
C2—C3—C4	119.89 (7)	C12—C13—C14	120.03 (9)
C2—C3—C7	119.70 (7)	C12—C13—H13	120.9 (8)
C4—C3—C7	120.41 (7)	C14—C13—H13	119.0 (8)
C5—C4—C3	119.91 (8)	C13—C14—C9	120.28 (8)
C5—C4—H4	120.0 (7)	C13—C14—H14	119.3 (7)
C3—C4—H4	120.0 (7)	C9—C14—H14	120.4 (7)
C4—C5—C6	120.76 (8)	N4—C15—C16	112.08 (7)
C4—C5—H5	120.5 (7)	N4—C15—H151	107.2 (7)
C6—C5—H5	118.7 (7)	C16—C15—H151	111.9 (7)
C5—C6—C1	118.81 (8)	N4—C15—H152	106.3 (7)
C5—C6—H6	121.1 (7)	C16—C15—H152	112.9 (7)
C1—C6—H6	120.0 (7)	H151—C15—H152	106.1 (10)
N2—N1—C1	116.36 (7)	C17—C16—C21	119.39 (8)
N2—N1—N1ⁱ	153.58 (7)	C17—C16—C15	120.55 (8)
C1—N1—N1ⁱ	90.02 (5)	C21—C16—C15	120.06 (8)
N3—N2—N1	172.98 (10)	C18—C17—C16	120.43 (9)
C15—N4—C8	113.00 (7)	C18—C17—H17	120.0 (7)
C15—N4—H02	111.5 (8)	C16—C17—H17	119.5 (7)
C8—N4—H02	105.5 (8)	C19—C18—C17	119.98 (9)
C15—N4—H01	109.6 (8)	C19—C18—H18	119.8 (8)
C8—N4—H01	111.9 (8)	C17—C18—H18	120.2 (8)
H02—N4—H01	105.0 (11)	C18—C19—C20	119.93 (9)
N4—C8—C9	113.58 (6)	C18—C19—H19	119.6 (8)
N4—C8—H81	105.7 (7)	C20—C19—H19	120.5 (8)
C9—C8—H81	111.4 (7)	C19—C20—C21	120.27 (9)
N4—C8—H82	105.7 (7)	C19—C20—H20	121.2 (8)
C9—C8—H82	112.5 (7)	C21—C20—H20	118.5 (8)
H81—C8—H82	107.5 (9)	C20—C21—C16	120.00 (9)
C14—C9—C10	119.25 (8)	C20—C21—H21	120.1 (7)
C14—C9—C8	120.41 (7)	C16—C21—H21	119.8 (7)
C10—C9—C8	120.33 (7)

C6—C1—C2—C3	−1.03 (12)	N4—C8—C9—C14	−94.60 (9)
N1—C1—C2—C3	−179.70 (7)	N4—C8—C9—C10	86.36 (9)
C1—C2—C3—C4	0.77 (12)	C14—C9—C10—C11	0.67 (13)
C1—C2—C3—C7	−179.64 (7)	C8—C9—C10—C11	179.72 (8)
O1—C7—C3—C2	−166.55 (7)	C9—C10—C11—C12	−0.63 (14)
O2—C7—C3—C2	14.11 (11)	C10—C11—C12—C13	0.24 (14)
O1—C7—C3—C4	13.04 (11)	C11—C12—C13—C14	0.11 (14)
O2—C7—C3—C4	−166.31 (7)	C12—C13—C14—C9	−0.07 (14)
C2—C3—C4—C5	0.11 (12)	C10—C9—C14—C13	−0.32 (13)
C7—C3—C4—C5	−179.47 (7)	C8—C9—C14—C13	−179.37 (8)
C3—C4—C5—C6	−0.76 (13)	C8—N4—C15—C16	−173.66 (7)
C4—C5—C6—C1	0.51 (13)	N4—C15—C16—C17	−109.06 (9)
C2—C1—C6—C5	0.40 (13)	N4—C15—C16—C21	71.97 (10)
N1—C1—C6—C5	178.95 (8)	C21—C16—C17—C18	0.17 (13)
C2—C1—N1—N2	−167.14 (8)	C15—C16—C17—C18	−178.81 (8)
C6—C1—N1—N2	14.23 (13)	C16—C17—C18—C19	−0.12 (14)
C2—C1—N1—N1ⁱ	14.32 (8)	C17—C18—C19—C20	−0.11 (14)
C6—C1—N1—N1ⁱ	−164.30 (7)	C18—C19—C20—C21	0.30 (14)
C1—N1—N2—N3	177.0 (8)	C19—C20—C21—C16	−0.25 (13)
N1ⁱ—N1—N2—N3	−6.3 (9)	C17—C16—C21—C20	0.02 (13)
C15—N4—C8—C9	−69.24 (9)	C15—C16—C21—C20	179.00 (8)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H01···O1	0.946 (14)	1.809 (14)	2.7228 (10)	161.5 (11)
N4—H02···O2ⁱⁱ	0.986 (13)	1.746 (14)	2.7103 (11)	164.8 (13)

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

Dicyclohexylammonium 3-azidebenzoate (3a-dc-i) top

Crystal data top

C₁₉H₂₈N₄O₂	Z = 2
M_r = 344.45	F(000) = 372
Triclinic, P1	D_x = 1.259 Mg m⁻³
a = 9.1925 (5) Å	Melting point: not measured K
b = 10.1813 (5) Å	Mo Kα radiation, λ = 0.71073 Å
c = 11.3543 (6) Å	Cell parameters from 6022 reflections
α = 110.816 (1)°	µ = 0.08 mm⁻¹
β = 103.168 (2)°	T = 82 K
γ = 103.370 (1)°	Plate, pale-yellow
V = 908.51 (8) Å³	0.44 × 0.38 × 0.26 mm

Data collection top

Bruker SMART CCD area detector system diffractometer	5259 independent reflections
Radiation source: rotating anode	4561 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 30.0°, θ_min = 2.3°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −12→12
T_min = 0.964, T_max = 0.979	k = −14→14
14513 measured reflections	l = −15→15

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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.100	Only H-atom coordinates refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0603P)² + 0.1086P] where P = (F_o² + 2F_c²)/3
5259 reflections	(Δ/σ)_max < 0.001
312 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C7	0.70855 (8)	0.21243 (8)	0.35622 (7)	0.01268 (14)
C1	0.32743 (9)	−0.12205 (8)	0.23699 (8)	0.01447 (15)
C2	0.45174 (9)	0.01540 (8)	0.31880 (7)	0.01310 (14)
H2	0.4580 (13)	0.0764 (12)	0.4099 (11)	0.016*
C3	0.57277 (8)	0.06267 (8)	0.27095 (7)	0.01286 (14)
C4	0.56854 (9)	−0.02721 (9)	0.14289 (8)	0.01656 (15)
H4	0.6537 (14)	0.0086 (13)	0.1104 (11)	0.020*
C5	0.44280 (10)	−0.16295 (9)	0.06162 (8)	0.01891 (16)
H5	0.4334 (14)	−0.2283 (13)	−0.0342 (12)	0.023*
C6	0.32247 (10)	−0.21067 (9)	0.10857 (8)	0.01750 (15)
H6	0.2340 (14)	−0.3066 (13)	0.0532 (11)	0.021*
O1	0.70011 (7)	0.29827 (6)	0.46504 (6)	0.01637 (12)
O2	0.81882 (7)	0.23951 (7)	0.30949 (6)	0.01751 (13)
N1	0.19848 (8)	−0.18239 (8)	0.27522 (7)	0.01976 (15)
N2	0.19097 (8)	−0.10182 (8)	0.38449 (7)	0.01736 (14)
N3	0.16737 (9)	−0.04166 (8)	0.48004 (8)	0.02245 (16)
C8	0.19607 (8)	0.33539 (8)	0.51332 (7)	0.01066 (13)
H8	0.1478 (13)	0.2249 (12)	0.4671 (10)	0.013*
C9	0.37823 (8)	0.38432 (8)	0.56345 (7)	0.01276 (14)
H91	0.4184 (13)	0.4932 (12)	0.5983 (10)	0.015*
H92	0.4197 (13)	0.3430 (12)	0.4900 (11)	0.015*
C10	0.43700 (9)	0.33466 (9)	0.67339 (8)	0.01423 (14)
H101	0.3959 (13)	0.2232 (13)	0.6352 (11)	0.017*
H102	0.5546 (13)	0.3669 (12)	0.7044 (11)	0.017*
C11	0.37735 (10)	0.39622 (9)	0.79020 (8)	0.01746 (15)
H111	0.4231 (14)	0.5096 (13)	0.8321 (12)	0.021*
H112	0.4142 (14)	0.3637 (13)	0.8620 (11)	0.021*
C12	0.19439 (10)	0.34459 (10)	0.73900 (8)	0.01672 (15)
H121	0.1516 (14)	0.2336 (13)	0.7038 (11)	0.020*
H122	0.1563 (14)	0.3861 (13)	0.8138 (11)	0.020*
C13	0.13321 (9)	0.39282 (8)	0.62883 (7)	0.01319 (14)
H131	0.0127 (13)	0.3532 (12)	0.5901 (11)	0.016*
H132	0.1684 (13)	0.5036 (12)	0.6655 (11)	0.016*
C14	0.18670 (8)	0.35429 (8)	0.29082 (7)	0.01063 (13)
H14	0.3007 (13)	0.4071 (12)	0.3229 (10)	0.013*
C15	0.09930 (9)	0.41119 (8)	0.19752 (7)	0.01276 (14)
H151	0.1219 (13)	0.5200 (12)	0.2462 (11)	0.015*
H152	−0.0179 (13)	0.3587 (12)	0.1705 (11)	0.015*
C16	0.14699 (9)	0.37695 (9)	0.07112 (7)	0.01443 (14)
H161	0.0811 (13)	0.4088 (13)	0.0098 (11)	0.017*
H162	0.2609 (14)	0.4398 (13)	0.0977 (11)	0.017*
C17	0.12389 (10)	0.21029 (9)	−0.00144 (8)	0.01670 (15)
H171	0.1639 (14)	0.1907 (13)	−0.0790 (11)	0.020*
H172	0.0067 (14)	0.1506 (13)	−0.0381 (12)	0.020*
C18	0.20933 (10)	0.15616 (9)	0.09535 (8)	0.01642 (15)
H181	0.3260 (14)	0.2096 (13)	0.1283 (11)	0.020*
H182	0.1905 (14)	0.0468 (13)	0.0484 (11)	0.020*
C19	0.15390 (9)	0.18612 (8)	0.21759 (7)	0.01370 (14)
H191	0.0384 (13)	0.1314 (12)	0.1899 (11)	0.016*
H192	0.2127 (13)	0.1476 (12)	0.2772 (11)	0.016*
N4	0.13682 (7)	0.39406 (7)	0.41333 (6)	0.01020 (12)
H1N	0.0246 (14)	0.3568 (13)	0.3842 (11)	0.021 (3)*
H2N	0.1767 (15)	0.4977 (14)	0.4572 (12)	0.024 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.0105 (3)	0.0118 (3)	0.0152 (3)	0.0034 (2)	0.0029 (2)	0.0064 (3)
C1	0.0116 (3)	0.0134 (3)	0.0187 (3)	0.0038 (3)	0.0033 (3)	0.0086 (3)
C2	0.0120 (3)	0.0120 (3)	0.0148 (3)	0.0043 (3)	0.0034 (2)	0.0058 (3)
C3	0.0112 (3)	0.0111 (3)	0.0154 (3)	0.0041 (2)	0.0030 (2)	0.0055 (3)
C4	0.0160 (3)	0.0153 (3)	0.0170 (3)	0.0046 (3)	0.0064 (3)	0.0055 (3)
C5	0.0205 (4)	0.0151 (3)	0.0160 (3)	0.0045 (3)	0.0047 (3)	0.0030 (3)
C6	0.0158 (3)	0.0132 (3)	0.0185 (4)	0.0028 (3)	0.0019 (3)	0.0052 (3)
O1	0.0164 (3)	0.0126 (2)	0.0173 (3)	0.0034 (2)	0.0064 (2)	0.0039 (2)
O2	0.0123 (3)	0.0191 (3)	0.0184 (3)	0.0019 (2)	0.0060 (2)	0.0069 (2)
N1	0.0162 (3)	0.0162 (3)	0.0223 (3)	−0.0001 (2)	0.0064 (3)	0.0070 (3)
N2	0.0125 (3)	0.0150 (3)	0.0246 (3)	0.0023 (2)	0.0050 (2)	0.0110 (3)
N3	0.0203 (3)	0.0193 (3)	0.0278 (4)	0.0050 (3)	0.0097 (3)	0.0103 (3)
C8	0.0106 (3)	0.0121 (3)	0.0108 (3)	0.0042 (2)	0.0038 (2)	0.0063 (2)
C9	0.0102 (3)	0.0156 (3)	0.0145 (3)	0.0049 (3)	0.0044 (2)	0.0083 (3)
C10	0.0124 (3)	0.0163 (3)	0.0148 (3)	0.0054 (3)	0.0031 (3)	0.0083 (3)
C11	0.0176 (3)	0.0216 (4)	0.0131 (3)	0.0070 (3)	0.0031 (3)	0.0085 (3)
C12	0.0177 (3)	0.0233 (4)	0.0151 (3)	0.0088 (3)	0.0080 (3)	0.0121 (3)
C13	0.0134 (3)	0.0167 (3)	0.0128 (3)	0.0066 (3)	0.0064 (3)	0.0080 (3)
C14	0.0108 (3)	0.0118 (3)	0.0100 (3)	0.0039 (2)	0.0044 (2)	0.0049 (2)
C15	0.0151 (3)	0.0138 (3)	0.0121 (3)	0.0067 (3)	0.0054 (2)	0.0069 (3)
C16	0.0173 (3)	0.0154 (3)	0.0125 (3)	0.0055 (3)	0.0063 (3)	0.0073 (3)
C17	0.0223 (4)	0.0163 (3)	0.0117 (3)	0.0067 (3)	0.0072 (3)	0.0054 (3)
C18	0.0223 (4)	0.0160 (3)	0.0150 (3)	0.0099 (3)	0.0100 (3)	0.0066 (3)
C19	0.0177 (3)	0.0129 (3)	0.0132 (3)	0.0072 (3)	0.0073 (3)	0.0060 (3)
N4	0.0104 (3)	0.0112 (3)	0.0101 (3)	0.0042 (2)	0.0041 (2)	0.0051 (2)

Geometric parameters (Å, º) top

C7—O1	1.2665 (9)	C11—H111	1.015 (12)
C7—O2	1.2668 (9)	C11—H112	1.003 (12)
C7—C3	1.5298 (10)	C12—C13	1.5382 (10)
C1—C6	1.3993 (11)	C12—H121	0.997 (12)
C1—C2	1.4071 (10)	C12—H122	0.986 (11)
C1—N1	1.4346 (10)	C13—H131	1.014 (11)
C2—C3	1.4065 (10)	C13—H132	0.993 (11)
C2—H2	0.979 (11)	C14—N4	1.5116 (9)
C3—C4	1.4019 (10)	C14—C19	1.5327 (10)
C4—C5	1.4023 (11)	C14—C15	1.5386 (10)
C4—H4	0.989 (12)	C14—H14	0.973 (11)
C5—C6	1.3957 (12)	C15—C16	1.5412 (10)
C5—H5	1.025 (11)	C15—H151	0.991 (11)
C6—H6	0.987 (12)	C15—H152	1.004 (11)
N1—N2	1.2486 (10)	C16—C17	1.5372 (11)
N2—N3	1.1382 (11)	C16—H161	1.008 (11)
C8—N4	1.5143 (9)	C16—H162	1.003 (12)
C8—C13	1.5337 (10)	C17—C18	1.5381 (11)
C8—C9	1.5344 (10)	C17—H171	1.003 (11)
C8—H8	0.991 (11)	C17—H172	1.008 (12)
C9—C10	1.5406 (10)	C18—C19	1.5402 (10)
C9—H91	0.976 (11)	C18—H181	0.994 (12)
C9—H92	0.994 (11)	C18—H182	1.000 (11)
C10—C11	1.5337 (11)	C19—H191	0.994 (11)
C10—H101	0.998 (11)	C19—H192	1.012 (11)
C10—H102	0.990 (11)	N4—H1N	0.944 (12)
C11—C12	1.5399 (11)	N4—H2N	0.928 (13)

O1—C7—O2	126.05 (7)	C11—C12—H122	110.0 (7)
O1—C7—C3	117.77 (6)	H121—C12—H122	107.0 (9)
O2—C7—C3	116.18 (7)	C6—C13—C12	111.18 (6)
C6—C1—C2	120.65 (7)	C6—C13—H131	107.8 (6)
C6—C1—N1	114.95 (7)	C12—C13—H131	111.6 (6)
C2—C1—N1	124.40 (7)	C6—C13—H132	108.1 (6)
C3—C2—C1	119.36 (7)	C12—C13—H132	110.5 (6)
C3—C2—H2	119.4 (6)	H131—C13—H132	107.6 (9)
C1—C2—H2	121.1 (6)	N4—C14—C19	112.60 (6)
C4—C3—C2	119.87 (7)	N4—C14—C15	108.14 (5)
C4—C3—C7	119.28 (7)	C19—C14—C15	111.00 (6)
C2—C3—C7	120.84 (7)	N4—C14—H14	106.2 (6)
C3—C4—C5	120.20 (7)	C19—C14—H14	108.9 (6)
C3—C4—H4	118.7 (7)	C15—C14—H14	109.9 (6)
C5—C4—H4	121.0 (7)	C14—C15—C16	111.01 (6)
C6—C5—C4	120.22 (7)	C14—C15—H151	110.0 (6)
C6—C5—H5	117.8 (7)	C16—C15—H151	110.6 (6)
C4—C5—H5	121.9 (7)	C14—C15—H152	107.8 (6)
C5—C6—C1	119.68 (7)	C16—C15—H152	109.3 (6)
C5—C6—H6	121.2 (7)	H151—C15—H152	108.1 (9)
C1—C6—H6	119.1 (7)	C17—C16—C15	111.83 (6)
N2—N1—C1	117.16 (7)	C17—C16—H161	110.5 (6)
N3—N2—N1	171.75 (8)	C15—C16—H161	108.4 (6)
N4—C8—C13	107.56 (5)	C17—C16—H162	110.2 (6)
N4—C8—C9	111.33 (6)	C15—C16—H162	108.8 (6)
C13—C8—C9	111.57 (6)	H161—C16—H162	106.9 (9)
N4—C8—H8	107.0 (6)	C16—C17—C18	110.97 (6)
C13—C8—H8	108.5 (6)	C16—C17—H171	111.2 (7)
C9—C8—H8	110.7 (6)	C18—C17—H171	109.5 (7)
C6—C9—C10	110.60 (6)	C16—C17—H172	108.8 (7)
C6—C9—H91	106.7 (6)	C18—C17—H172	108.7 (7)
C10—C9—H91	110.9 (6)	H171—C17—H172	107.7 (9)
C6—C9—H92	112.1 (6)	C17—C18—C19	111.51 (6)
C10—C9—H92	108.8 (6)	C17—C18—H181	109.7 (7)
H91—C9—H92	107.7 (9)	C19—C18—H181	108.2 (6)
C11—C10—C9	111.16 (6)	C17—C18—H182	110.6 (7)
C11—C10—H101	108.2 (6)	C19—C18—H182	109.4 (7)
C9—C10—H101	109.4 (6)	H181—C18—H182	107.4 (9)
C11—C10—H102	111.3 (6)	C14—C19—C18	109.03 (6)
C9—C10—H102	109.5 (7)	C14—C19—H191	109.1 (6)
H101—C10—H102	107.2 (9)	C18—C19—H191	111.1 (6)
C10—C11—C12	110.10 (6)	C14—C19—H192	111.9 (6)
C10—C11—H111	108.5 (7)	C18—C19—H192	108.2 (6)
C12—C11—H111	109.6 (7)	H191—C19—H192	107.5 (9)
C10—C11—H112	111.8 (6)	C14—N4—C6	117.34 (5)
C12—C11—H112	109.5 (7)	C14—N4—H1N	108.1 (7)
H111—C11—H112	107.3 (9)	C6—N4—H1N	106.9 (7)
C13—C12—C11	111.07 (6)	C14—N4—H2N	105.4 (7)
C13—C12—H121	110.3 (7)	C6—N4—H2N	107.6 (7)
C11—C12—H121	108.5 (7)	H1N—N4—H2N	111.7 (10)
C13—C12—H122	109.8 (7)

C6—C1—C2—C3	−0.73 (11)	C8—C9—C10—C11	−56.76 (8)
N1—C1—C2—C3	179.46 (7)	C9—C10—C11—C12	57.53 (8)
C1—C2—C3—C4	−0.06 (11)	C10—C11—C12—C13	−56.87 (8)
C1—C2—C3—C7	179.13 (6)	N4—C8—C13—C12	−177.31 (6)
O1—C7—C3—C4	172.53 (7)	C9—C8—C13—C12	−54.94 (8)
O2—C7—C3—C4	−6.57 (10)	C11—C12—C13—C6	55.71 (8)
O1—C7—C3—C2	−6.66 (10)	N4—C14—C15—C16	178.95 (6)
O2—C7—C3—C2	174.24 (7)	C19—C14—C15—C16	−57.08 (8)
C2—C3—C4—C5	0.96 (12)	C14—C15—C16—C17	53.71 (8)
C7—C3—C4—C5	−178.24 (7)	C15—C16—C17—C18	−53.06 (8)
C3—C4—C5—C6	−1.09 (12)	C16—C17—C18—C19	55.98 (9)
C4—C5—C6—C1	0.30 (12)	N4—C14—C19—C18	−179.58 (6)
C2—C1—C6—C5	0.61 (12)	C15—C14—C19—C18	59.03 (8)
N1—C1—C6—C5	−179.57 (7)	C17—C18—C19—C14	−58.68 (8)
C6—C1—N1—N2	−174.40 (7)	C19—C14—N4—C8	51.17 (8)
C2—C1—N1—N2	5.42 (11)	C15—C14—N4—C8	174.17 (6)
C1—N1—N2—N3	175.5 (5)	C13—C6—N4—C14	178.82 (6)
N4—C8—C9—C10	175.39 (6)	O2—C6—N4—C14	56.30 (8)
C13—C8—C9—C10	55.21 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N···O2ⁱ	0.944 (12)	1.797 (12)	2.7194 (8)	164.9 (11)
N4—H2N···O1ⁱⁱ	0.928 (13)	1.879 (13)	2.7888 (8)	166.3 (11)

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

N-benzyl-2-phenylethylammonium 4-azidebenzoate (4a-bp-i) top

Crystal data top

C₂₂H₂₂N₄O₂	Z = 2
M_r = 374.44	F(000) = 396
Triclinic, P1	D_x = 1.253 Mg m⁻³
a = 8.0615 (2) Å	Melting point: not measured K
b = 10.3615 (2) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.5356 (4) Å	Cell parameters from 6018 reflections
α = 72.503 (1)°	µ = 0.08 mm⁻¹
β = 72.933 (1)°	T = 92 K
γ = 70.506 (1)°	Plate, pale-yellow
V = 992.76 (4) Å³	0.31 × 0.12 × 0.08 mm

Data collection top

Bruker SMART CCD area detector system diffractometer	5766 independent reflections
Radiation source: rotating anode	4057 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 30.0°, θ_min = 1.6°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −11→11
T_min = 0.975, T_max = 0.993	k = −14→14
15962 measured reflections	l = −18→18

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)] = 0.050	Hydrogen site location: difference Fourier map
wR(F²) = 0.148	Only H-atom coordinates refined
S = 1.03	w = 1/[σ²(F_o²) + (0.0855P)²] where P = (F_o² + 2F_c²)/3
5766 reflections	(Δ/σ)_max < 0.001
319 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.74869 (15)	−0.00293 (12)	0.52514 (9)	0.0230 (2)
C2	0.66148 (16)	0.10149 (12)	0.58242 (9)	0.0245 (2)
H2	0.567 (2)	0.1882 (15)	0.5564 (11)	0.029*
C3	0.70655 (16)	0.08587 (12)	0.67811 (9)	0.0243 (2)
H3	0.650 (2)	0.1543 (16)	0.7150 (12)	0.029*
C4	0.83763 (15)	−0.03191 (12)	0.71663 (9)	0.0230 (2)
C5	0.92501 (16)	−0.13450 (12)	0.65719 (9)	0.0241 (2)
H5	1.020 (2)	−0.2167 (15)	0.6795 (12)	0.029*
C6	0.87929 (16)	−0.12180 (12)	0.56236 (9)	0.0241 (2)
H6	0.939 (2)	−0.1914 (16)	0.5195 (12)	0.029*
C7	0.88465 (18)	−0.04706 (13)	0.82082 (9)	0.0282 (3)
N1	0.71091 (15)	0.00314 (11)	0.42634 (8)	0.0287 (2)
N2	0.61219 (15)	0.11711 (11)	0.38672 (8)	0.0293 (2)
N3	0.52390 (18)	0.21433 (12)	0.34259 (10)	0.0391 (3)
O2	0.77098 (14)	0.02808 (10)	0.88220 (7)	0.0383 (2)
O1	1.03312 (14)	−0.13148 (10)	0.83829 (8)	0.0389 (3)
N4	0.75323 (14)	0.07712 (10)	0.06816 (8)	0.0262 (2)
H01	0.792 (2)	0.0517 (15)	−0.0021 (12)	0.031*
H02	0.844 (2)	0.0990 (16)	0.0848 (12)	0.031*
C9	0.66866 (16)	0.33067 (13)	−0.01742 (10)	0.0288 (3)
C10	0.64991 (18)	0.35859 (14)	−0.12205 (10)	0.0343 (3)
H10	0.592 (2)	0.2991 (17)	−0.1427 (13)	0.041*
C11	0.7074 (2)	0.46757 (16)	−0.19835 (12)	0.0468 (4)
H11	0.696 (3)	0.489 (2)	−0.2740 (16)	0.056*
C12	0.7841 (2)	0.54888 (17)	−0.17177 (16)	0.0564 (5)
H12	0.825 (3)	0.621 (2)	−0.2236 (17)	0.068*
C13	0.8065 (2)	0.52141 (16)	−0.06864 (18)	0.0535 (5)
H13	0.862 (3)	0.570 (2)	−0.0520 (17)	0.064*
C14	0.74753 (19)	0.41174 (15)	0.00941 (13)	0.0399 (3)
H14	0.766 (2)	0.3941 (19)	0.0821 (15)	0.048*
C8	0.60335 (18)	0.21146 (13)	0.06385 (10)	0.0316 (3)
H81	0.567 (2)	0.2277 (17)	0.1372 (13)	0.038*
H82	0.495 (2)	0.1929 (17)	0.0431 (12)	0.038*
C17	0.81127 (16)	−0.29394 (12)	0.24357 (10)	0.0281 (3)
C18	0.8430 (2)	−0.30448 (14)	0.34206 (11)	0.0358 (3)
H18	0.895 (2)	−0.2346 (18)	0.3501 (13)	0.043*
C19	0.8016 (2)	−0.41065 (17)	0.42900 (13)	0.0523 (5)
H19	0.822 (3)	−0.417 (2)	0.4979 (17)	0.063*
C20	0.7294 (2)	−0.50740 (18)	0.41942 (19)	0.0646 (6)
H20	0.700 (3)	−0.582 (2)	0.4825 (18)	0.078*
C21	0.6957 (2)	−0.49794 (18)	0.3224 (2)	0.0662 (6)
H21	0.649 (3)	−0.554 (2)	0.3083 (18)	0.079*
C22	0.7375 (2)	−0.39237 (16)	0.23419 (16)	0.0444 (4)
H22	0.717 (3)	−0.385 (2)	0.1652 (16)	0.053*
C15	0.69815 (18)	−0.04372 (13)	0.15029 (10)	0.0293 (3)
H151	0.585 (2)	−0.0544 (16)	0.1329 (12)	0.035*
H152	0.669 (2)	−0.0169 (16)	0.2163 (13)	0.035*
C16	0.85513 (18)	−0.17717 (13)	0.15046 (10)	0.0303 (3)
H161	0.883 (2)	−0.2081 (16)	0.0809 (13)	0.036*
H162	0.963 (2)	−0.1550 (16)	0.1562 (12)	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0226 (5)	0.0246 (5)	0.0209 (5)	−0.0098 (4)	−0.0045 (4)	−0.0001 (4)
C2	0.0215 (5)	0.0216 (5)	0.0255 (6)	−0.0042 (4)	−0.0057 (4)	0.0007 (4)
C3	0.0244 (6)	0.0211 (5)	0.0228 (5)	−0.0045 (4)	−0.0026 (4)	−0.0026 (4)
C4	0.0227 (5)	0.0219 (5)	0.0200 (5)	−0.0064 (4)	−0.0032 (4)	0.0007 (4)
C5	0.0220 (5)	0.0206 (5)	0.0248 (5)	−0.0044 (4)	−0.0056 (4)	0.0009 (4)
C6	0.0242 (6)	0.0214 (5)	0.0243 (6)	−0.0055 (4)	−0.0040 (4)	−0.0036 (4)
C7	0.0357 (7)	0.0236 (6)	0.0209 (5)	−0.0057 (5)	−0.0082 (5)	0.0009 (4)
N1	0.0320 (6)	0.0281 (5)	0.0259 (5)	−0.0076 (4)	−0.0114 (4)	−0.0014 (4)
N2	0.0349 (6)	0.0298 (5)	0.0265 (5)	−0.0153 (5)	−0.0114 (4)	0.0011 (4)
N3	0.0501 (7)	0.0320 (6)	0.0376 (6)	−0.0148 (5)	−0.0228 (6)	0.0058 (5)
O2	0.0447 (6)	0.0398 (5)	0.0234 (4)	−0.0029 (4)	−0.0062 (4)	−0.0079 (4)
O1	0.0459 (6)	0.0335 (5)	0.0330 (5)	0.0041 (4)	−0.0219 (4)	−0.0048 (4)
N4	0.0259 (5)	0.0245 (5)	0.0178 (5)	−0.0002 (4)	−0.0026 (4)	0.0005 (4)
C9	0.0233 (6)	0.0240 (6)	0.0252 (6)	0.0047 (4)	−0.0041 (5)	0.0009 (4)
C10	0.0295 (7)	0.0316 (6)	0.0258 (6)	0.0044 (5)	−0.0053 (5)	0.0013 (5)
C11	0.0377 (8)	0.0379 (8)	0.0320 (7)	0.0070 (6)	0.0021 (6)	0.0104 (6)
C12	0.0310 (8)	0.0315 (8)	0.0684 (12)	0.0031 (6)	0.0046 (7)	0.0153 (7)
C13	0.0285 (7)	0.0268 (7)	0.0977 (15)	0.0002 (6)	−0.0153 (8)	−0.0103 (8)
C14	0.0323 (7)	0.0282 (7)	0.0520 (9)	0.0066 (5)	−0.0165 (6)	−0.0078 (6)
C8	0.0295 (6)	0.0259 (6)	0.0236 (6)	0.0035 (5)	−0.0020 (5)	0.0010 (5)
C17	0.0228 (6)	0.0193 (5)	0.0326 (6)	0.0004 (4)	−0.0015 (5)	−0.0035 (4)
C18	0.0395 (8)	0.0262 (6)	0.0296 (7)	−0.0016 (5)	−0.0019 (5)	−0.0025 (5)
C19	0.0480 (9)	0.0371 (8)	0.0366 (8)	0.0059 (7)	0.0039 (7)	0.0097 (6)
C20	0.0380 (9)	0.0334 (8)	0.0794 (14)	−0.0006 (7)	0.0051 (9)	0.0213 (8)
C21	0.0365 (9)	0.0282 (8)	0.123 (2)	−0.0134 (7)	−0.0122 (10)	−0.0019 (10)
C22	0.0313 (7)	0.0326 (7)	0.0693 (11)	−0.0049 (6)	−0.0151 (7)	−0.0114 (7)
C15	0.0299 (6)	0.0249 (6)	0.0219 (6)	−0.0019 (5)	−0.0008 (5)	−0.0001 (4)
C16	0.0292 (7)	0.0250 (6)	0.0254 (6)	−0.0006 (5)	−0.0004 (5)	−0.0022 (5)

Geometric parameters (Å, º) top

C1—C2	1.3938 (17)	C11—H11	1.005 (19)
C1—C6	1.3971 (16)	C12—C13	1.392 (3)
C1—N1	1.4356 (15)	C12—H12	0.93 (2)
C2—C3	1.3952 (17)	C13—C14	1.406 (2)
C2—H2	1.010 (14)	C13—H13	0.88 (2)
C3—C4	1.3992 (16)	C14—H14	0.993 (18)
C3—H3	0.907 (15)	C8—H81	0.998 (16)
C4—C5	1.3983 (17)	C8—H82	1.079 (16)
C4—C7	1.5159 (16)	C17—C22	1.392 (2)
C5—C6	1.3945 (17)	C17—C18	1.396 (2)
C5—H5	0.976 (15)	C17—C16	1.5114 (17)
C6—H6	0.972 (15)	C18—C19	1.394 (2)
C7—O1	1.2636 (15)	C18—H18	0.993 (17)
C7—O2	1.2657 (15)	C19—C20	1.369 (3)
N1—N2	1.2482 (14)	C19—H19	0.98 (2)
N2—N3	1.1346 (15)	C20—C21	1.386 (3)
N4—C15	1.4983 (16)	C20—H20	0.99 (2)
N4—C8	1.5069 (15)	C21—C22	1.400 (3)
N4—H01	0.996 (15)	C21—H21	0.88 (2)
N4—H02	0.938 (16)	C22—H22	0.971 (19)
C9—C14	1.385 (2)	C15—C16	1.5315 (17)
C9—C10	1.4009 (18)	C15—H151	1.054 (16)
C9—C8	1.5133 (18)	C15—H152	0.955 (16)
C10—C11	1.387 (2)	C16—H161	1.025 (16)
C10—H10	1.022 (17)	C16—H162	0.996 (16)
C11—C12	1.372 (3)

C2—C1—C6	120.93 (10)	C12—C13—H13	120.7 (14)
C2—C1—N1	123.11 (10)	C14—C13—H13	119.1 (14)
C6—C1—N1	115.96 (10)	C9—C14—C13	119.47 (15)
C1—C2—C3	118.96 (10)	C9—C14—H14	122.2 (10)
C1—C2—H2	121.8 (8)	C13—C14—H14	118.4 (11)
C3—C2—H2	119.2 (8)	N4—C8—C9	110.35 (10)
C2—C3—C4	121.10 (11)	N4—C8—H81	105.1 (9)
C2—C3—H3	118.8 (9)	C9—C8—H81	112.2 (9)
C4—C3—H3	120.1 (9)	N4—C8—H82	107.0 (9)
C5—C4—C3	118.95 (11)	C9—C8—H82	110.9 (8)
C5—C4—C7	120.72 (10)	H81—C8—H82	111.0 (13)
C3—C4—C7	120.33 (10)	C22—C17—C18	118.34 (13)
C6—C5—C4	120.68 (10)	C22—C17—C16	121.45 (13)
C6—C5—H5	117.4 (8)	C18—C17—C16	120.20 (12)
C4—C5—H5	121.9 (8)	C19—C18—C17	120.93 (16)
C5—C6—C1	119.35 (11)	C19—C18—H18	119.8 (10)
C5—C6—H6	122.1 (9)	C17—C18—H18	119.3 (10)
C1—C6—H6	118.5 (9)	C20—C19—C18	120.56 (18)
O1—C7—O2	125.90 (11)	C20—C19—H19	118.9 (12)
O1—C7—C4	117.71 (11)	C18—C19—H19	120.5 (12)
O2—C7—C4	116.38 (11)	C19—C20—C21	119.30 (16)
N2—N1—C1	115.54 (10)	C19—C20—H20	119.2 (13)
N3—N2—N1	172.92 (13)	C21—C20—H20	121.5 (13)
C15—N4—C8	112.72 (9)	C20—C21—C22	120.81 (18)
C15—N4—H01	108.1 (9)	C20—C21—H21	126.2 (16)
C8—N4—H01	109.5 (9)	C22—C21—H21	113.0 (16)
C15—N4—H02	110.7 (9)	C17—C22—C21	120.06 (18)
C8—N4—H02	103.8 (9)	C17—C22—H22	117.8 (11)
H01—N4—H02	112.0 (13)	C21—C22—H22	122.2 (11)
C14—C9—C10	119.50 (13)	N4—C15—C16	110.34 (10)
C14—C9—C8	121.36 (12)	N4—C15—H151	107.1 (8)
C10—C9—C8	119.15 (13)	C16—C15—H151	112.5 (9)
C11—C10—C9	120.61 (15)	N4—C15—H152	104.9 (9)
C11—C10—H10	119.3 (9)	C16—C15—H152	109.7 (9)
C9—C10—H10	120.1 (9)	H151—C15—H152	112.0 (13)
C12—C11—C10	120.03 (15)	C17—C16—C15	110.85 (10)
C12—C11—H11	118.0 (11)	C17—C16—H161	110.0 (9)
C10—C11—H11	122.0 (11)	C15—C16—H161	109.6 (9)
C11—C12—C13	120.22 (15)	C17—C16—H162	109.1 (9)
C11—C12—H12	119.7 (13)	C15—C16—H162	108.1 (9)
C13—C12—H12	120.0 (13)	H161—C16—H162	109.2 (13)
C12—C13—C14	120.17 (17)

C6—C1—C2—C3	0.04 (17)	C10—C11—C12—C13	0.8 (2)
N1—C1—C2—C3	179.60 (10)	C11—C12—C13—C14	−1.2 (2)
C1—C2—C3—C4	0.32 (18)	C10—C9—C14—C13	0.42 (18)
C2—C3—C4—C5	0.48 (17)	C8—C9—C14—C13	179.94 (12)
C2—C3—C4—C7	−179.95 (11)	C12—C13—C14—C9	0.6 (2)
C3—C4—C5—C6	−1.65 (17)	C15—N4—C8—C9	177.89 (11)
C7—C4—C5—C6	178.78 (11)	C14—C9—C8—N4	−88.51 (14)
C4—C5—C6—C1	2.01 (18)	C10—C9—C8—N4	91.01 (14)
C2—C1—C6—C5	−1.19 (17)	C22—C17—C18—C19	−0.1 (2)
N1—C1—C6—C5	179.22 (10)	C16—C17—C18—C19	179.34 (12)
C5—C4—C7—O1	18.61 (17)	C17—C18—C19—C20	0.2 (2)
C3—C4—C7—O1	−160.95 (12)	C18—C19—C20—C21	−0.7 (2)
C5—C4—C7—O2	−162.15 (12)	C19—C20—C21—C22	1.1 (3)
C3—C4—C7—O2	18.29 (17)	C18—C17—C22—C21	0.5 (2)
C2—C1—N1—N2	9.41 (17)	C16—C17—C22—C21	−178.98 (13)
C6—C1—N1—N2	−171.01 (11)	C20—C21—C22—C17	−0.9 (2)
C1—N1—N2—N3	−178.3 (10)	C8—N4—C15—C16	179.62 (11)
C14—C9—C10—C11	−0.83 (18)	C22—C17—C16—C15	93.70 (15)
C8—C9—C10—C11	179.64 (11)	C18—C17—C16—C15	−85.74 (15)
C9—C10—C11—C12	0.2 (2)	N4—C15—C16—C17	171.28 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H01···O2ⁱ	0.996 (15)	1.720 (15)	2.6689 (14)	157.8 (13)
N4—H02···O1ⁱⁱ	0.938 (16)	1.792 (16)	2.6914 (16)	159.8 (14)

Symmetry codes: (i) x, y, z−1; (ii) −x+2, −y, −z+1.

Dibenzylammonium 2-azidebenzoate (2a-db-f) top

Crystal data top

C₂₁H₂₀N₄O₂	F(000) = 760
M_r = 360.41	D_x = 1.255 Mg m⁻³
Monoclinic, Cc	Melting point: not measured K
a = 19.892 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.966 (2) Å	Cell parameters from 5377 reflections
c = 10.068 (2) Å	µ = 0.08 mm⁻¹
β = 107.06 (4)°	T = 88 K
V = 1908.1 (9) Å³	Bloc, orange
Z = 4	0.41 × 0.34 × 0.22 mm

Data collection top

Bruker SMART CCD area detector system diffractometer	2723 independent reflections
Radiation source: rotating anode	2511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 30.0°, θ_min = 2.3°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −27→19
T_min = 0.967, T_max = 0.982	k = −13→12
7279 measured reflections	l = −14→14

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.1113P)² + 0.0483P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2723 reflections	Δρ_max = 0.37 e Å⁻³
210 parameters	Δρ_min = −0.31 e Å⁻³
3 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: rigid model	Absolute structure parameter: 0 (10)

Special details top

Experimental. 'photo-irradiated product 2,1-benzisoxazolone is observed

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C8	0.41483 (7)	0.43225 (10)	0.49159 (7)	0.0248 (4)
H81	0.4084	0.4689	0.5785	0.030*
H82	0.3983	0.3380	0.4825	0.030*
C9	0.37055 (7)	0.51239 (9)	0.36955 (8)	0.0255 (4)
C10	0.32592 (7)	0.44757 (10)	0.25409 (8)	0.0277 (4)
H10	0.3248	0.3523	0.2507	0.033*
C11	0.28286 (7)	0.52154 (13)	0.14336 (9)	0.0331 (5)
H11	0.2522	0.4762	0.0662	0.040*
C12	0.28482 (8)	0.66108 (13)	0.14581 (14)	0.0390 (6)
H12	0.2555	0.7112	0.0708	0.047*
C13	0.32986 (8)	0.72615 (10)	0.25850 (17)	0.0590 (10)
H13	0.3323	0.8214	0.2593	0.071*
C14	0.37182 (7)	0.65333 (9)	0.37140 (14)	0.0525 (8)
H14	0.4013	0.6994	0.4496	0.063*
C15	0.53423 (7)	0.34853 (10)	0.61870 (9)	0.0234 (4)
H151	0.5216	0.2532	0.5978	0.028*
H152	0.5231	0.3725	0.7053	0.028*
C16	0.61217 (7)	0.36718 (9)	0.63952 (10)	0.0235 (4)
C17	0.64518 (7)	0.30437 (10)	0.55099 (12)	0.0276 (4)
H17	0.6186	0.2472	0.4792	0.033*
C18	0.71656 (7)	0.32468 (14)	0.56682 (14)	0.0318 (5)
H18	0.7382	0.2830	0.5050	0.038*
C19	0.75604 (7)	0.40676 (13)	0.67416 (17)	0.0416 (6)
H19	0.8045	0.4219	0.6849	0.050*
C20	0.72407 (7)	0.46625 (12)	0.76517 (16)	0.0509 (8)
H20	0.7512	0.5200	0.8396	0.061*
C21	0.65223 (7)	0.44763 (12)	0.74805 (12)	0.0381 (6)
H21	0.6307	0.4895	0.8100	0.046*
N4	0.49180 (7)	0.43511 (7)	0.50132 (8)	0.0201 (3)
H01	0.5071	0.5147	0.5226	0.023 (7)*
H02	0.4932	0.4150	0.4277	0.024 (7)*
C7	0.52571 (8)	0.28504 (8)	0.17894 (11)	0.0200 (5)	0.906 (6)
C1	0.51190 (8)	0.07364 (7)	0.31747 (11)	0.0189 (4)	0.906 (6)
C2	0.53695 (9)	−0.05179 (8)	0.37418 (14)	0.0225 (5)	0.906 (6)
H2	0.5113	−0.1020	0.4232	0.027*	0.906 (6)
C3	0.59934 (9)	−0.10279 (9)	0.35880 (16)	0.0249 (5)	0.906 (6)
H3	0.6165	−0.1870	0.3988	0.030*	0.906 (6)
C4	0.63682 (9)	−0.03081 (11)	0.28489 (17)	0.0245 (5)	0.906 (6)
H4	0.6797	−0.0651	0.2752	0.029*	0.906 (6)
C5	0.61046 (8)	0.09264 (10)	0.22511 (14)	0.0232 (5)	0.906 (6)
H5	0.6353	0.1404	0.1727	0.028*	0.906 (6)
C6	0.54822 (7)	0.14741 (8)	0.24074 (11)	0.0189 (4)	0.906 (6)
N1	0.44811 (8)	0.12950 (9)	0.33457 (13)	0.0269 (5)	0.906 (6)
N2	0.42273 (9)	0.06817 (12)	0.41648 (15)	0.0281 (6)	0.869 (8)
N3	0.39425 (10)	0.02378 (14)	0.48924 (18)	0.0403 (7)	0.869 (8)
O1	0.49965 (8)	0.36791 (7)	0.24507 (13)	0.0240 (4)	0.906 (6)
O2	0.53642 (9)	0.30931 (11)	0.06307 (12)	0.0255 (5)	0.906 (6)
C7P	0.5354 (14)	0.267 (3)	0.145 (3)	0.029 (3)*	0.105 (5)
C1P	0.5180 (8)	0.1133 (16)	0.2933 (18)	0.029 (3)*	0.105 (5)
C2P	0.5290 (9)	−0.0033 (17)	0.3724 (18)	0.029 (3)*	0.105 (5)
H2P	0.4998	−0.0233	0.4294	0.034*	0.105 (5)
C3P	0.5828 (10)	−0.0908 (15)	0.368 (2)	0.029 (3)*	0.105 (5)
H3P	0.5903	−0.1705	0.4221	0.034*	0.105 (5)
C4P	0.6255 (9)	−0.0615 (17)	0.285 (2)	0.029 (3)*	0.105 (5)
H4P	0.6623	−0.1212	0.2818	0.034*	0.105 (5)
C5P	0.6145 (9)	0.0552 (19)	0.2056 (19)	0.029 (3)*	0.105 (5)
H5P	0.6437	0.0752	0.1486	0.034*	0.105 (5)
C6P	0.5607 (9)	0.1426 (15)	0.2099 (18)	0.029 (3)*	0.105 (5)
N1P	0.4731 (18)	0.223 (4)	0.295 (4)	0.062 (8)*	0.105 (5)
N2P	0.3828 (14)	−0.026 (3)	0.527 (3)	0.055 (6)*	0.131 (8)
N3P	0.392 (2)	0.066 (4)	0.569 (4)	0.081 (10)*	0.131 (8)
O1P	0.4848 (12)	0.308 (3)	0.200 (2)	0.044 (5)*	0.105 (5)
O2P	0.5521 (15)	0.319 (3)	0.054 (3)	0.039 (6)*	0.105 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.0214 (8)	0.0259 (10)	0.0275 (9)	−0.0010 (7)	0.0079 (7)	−0.0026 (7)
C9	0.0192 (8)	0.0255 (10)	0.0315 (10)	0.0032 (7)	0.0068 (7)	−0.0034 (8)
C10	0.0258 (9)	0.0284 (11)	0.0280 (9)	−0.0031 (8)	0.0063 (7)	0.0010 (8)
C11	0.0247 (10)	0.0421 (14)	0.0309 (10)	−0.0019 (9)	0.0055 (8)	0.0039 (9)
C12	0.0259 (10)	0.0419 (14)	0.0453 (13)	0.0086 (9)	0.0043 (9)	0.0094 (11)
C13	0.0546 (17)	0.0287 (14)	0.072 (2)	0.0131 (13)	−0.0153 (15)	−0.0013 (14)
C14	0.0491 (16)	0.0261 (13)	0.0614 (18)	0.0088 (11)	−0.0164 (13)	−0.0088 (12)
C15	0.0243 (8)	0.0216 (9)	0.0225 (8)	−0.0020 (7)	0.0041 (6)	0.0023 (7)
C16	0.0227 (8)	0.0177 (9)	0.0268 (9)	0.0001 (6)	0.0020 (7)	0.0016 (7)
C17	0.0271 (10)	0.0295 (11)	0.0240 (9)	−0.0027 (8)	0.0039 (7)	0.0003 (7)
C18	0.0272 (10)	0.0326 (12)	0.0336 (11)	0.0031 (8)	0.0057 (8)	0.0032 (8)
C19	0.0215 (10)	0.0382 (14)	0.0596 (17)	0.0004 (9)	0.0031 (10)	−0.0078 (12)
C20	0.0256 (11)	0.0506 (17)	0.0667 (19)	−0.0014 (11)	−0.0017 (11)	−0.0301 (15)
C21	0.0272 (11)	0.0356 (13)	0.0459 (13)	0.0008 (9)	0.0018 (9)	−0.0187 (10)
N4	0.0188 (7)	0.0207 (8)	0.0202 (7)	0.0002 (6)	0.0046 (5)	−0.0013 (6)
C7	0.0223 (10)	0.0189 (11)	0.0181 (10)	0.0025 (7)	0.0048 (7)	0.0001 (8)
C1	0.0211 (9)	0.0156 (10)	0.0192 (9)	−0.0010 (7)	0.0046 (7)	−0.0005 (7)
C2	0.0274 (10)	0.0167 (11)	0.0219 (9)	0.0001 (8)	0.0050 (7)	0.0016 (8)
C3	0.0309 (13)	0.0196 (11)	0.0228 (10)	0.0055 (8)	0.0057 (8)	0.0008 (8)
C4	0.0254 (11)	0.0254 (12)	0.0227 (9)	0.0058 (9)	0.0071 (8)	−0.0014 (9)
C5	0.0267 (10)	0.0248 (11)	0.0188 (9)	0.0034 (8)	0.0079 (7)	−0.0026 (8)
C6	0.0214 (9)	0.0182 (10)	0.0167 (9)	0.0003 (7)	0.0049 (7)	−0.0006 (7)
N1	0.0235 (9)	0.0236 (10)	0.0360 (11)	−0.0003 (7)	0.0122 (8)	0.0032 (8)
N2	0.0225 (10)	0.0288 (12)	0.0328 (11)	−0.0017 (8)	0.0076 (8)	0.0012 (8)
N3	0.0317 (12)	0.0471 (17)	0.0467 (15)	−0.0029 (11)	0.0185 (10)	0.0112 (13)
O1	0.0309 (8)	0.0198 (8)	0.0223 (7)	0.0048 (6)	0.0094 (6)	−0.0006 (6)
O2	0.0373 (12)	0.0206 (9)	0.0210 (8)	0.0061 (8)	0.0122 (8)	0.0009 (6)

Geometric parameters (Å, º) top

C8—N4	1.5055	C7—O1	1.2636
C8—C9	1.5128	C7—O2	1.2691
C8—H81	0.9900	C7—C6	1.5185
C8—H82	0.9900	C1—C2	1.4035
C9—C10	1.3969	C1—C6	1.4094
C9—C14	1.4048	C1—N1	1.4414
C10—C11	1.3999	C2—C3	1.3910
C10—H10	0.9500	C2—H2	0.9500
C11—C12	1.3912	C3—C4	1.3964
C11—H11	0.9500	C3—H3	0.9500
C12—C13	1.3835	C4—C5	1.4020
C12—H12	0.9500	C4—H4	0.9500
C13—C14	1.3996	C5—C6	1.4036
C13—H13	0.9500	C5—H5	0.9500
C14—H14	0.9500	N1—N2	1.2462
C15—N4	1.5061	N2—N3	1.1387
C15—C16	1.5138	C7P—O2P	1.18 (4)
C15—H151	0.9900	C7P—O1P	1.35 (3)
C15—H152	0.9900	C7P—C6P	1.43 (3)
C16—C17	1.4003	C1P—C2P	1.3900
C16—C21	1.4004	C1P—C6P	1.3900
C17—C18	1.3963	C1P—N1P	1.42 (4)
C17—H17	0.9500	C2P—C3P	1.3900
C18—C19	1.3985	C2P—H2P	0.9500
C18—H18	0.9500	C3P—C4P	1.3900
C19—C20	1.3920	C3P—H3P	0.9500
C19—H19	0.9500	C4P—C5P	1.3900
C20—C21	1.4005	C4P—H4P	0.9500
C20—H20	0.9500	C5P—C6P	1.3900
C21—H21	0.9500	C5P—H5P	0.9500
N4—H01	0.8541	N1P—O1P	1.34 (4)
N4—H02	0.7767	N2P—N3P	1.00 (4)

N4—C8—C9	112.4	C15—N4—H01	105.0
N4—C8—H81	109.1	C8—N4—H02	104.7
C9—C8—H81	109.1	C15—N4—H02	115.6
N4—C8—H82	109.1	H01—N4—H02	111.6
C9—C8—H82	109.1	O1—C7—O2	124.4
H81—C8—H82	107.8	O1—C7—C6	119.4
C10—C9—C14	118.6	O2—C7—C6	116.1
C10—C9—C8	120.5	C2—C1—C6	120.6
C14—C9—C8	120.9	C2—C1—N1	121.0
C9—C10—C11	120.7	C6—C1—N1	118.3
C9—C10—H10	119.7	C3—C2—C1	120.1
C11—C10—H10	119.7	C3—C2—H2	119.9
C12—C11—C10	120.3	C1—C2—H2	119.9
C12—C11—H11	119.8	C2—C3—C4	120.3
C10—C11—H11	119.8	C2—C3—H3	119.8
C13—C12—C11	119.4	C4—C3—H3	119.8
C13—C12—H12	120.3	C3—C4—C5	119.3
C11—C12—H12	120.3	C3—C4—H4	120.4
C12—C13—C14	120.8	C5—C4—H4	120.4
C12—C13—H13	119.6	C4—C5—C6	121.6
C14—C13—H13	119.6	C4—C5—H5	119.2
C13—C14—C9	120.2	C6—C5—H5	119.2
C13—C14—H14	119.9	C5—C6—C1	118.0
C9—C14—H14	119.9	C5—C6—C7	118.0
N4—C15—C16	110.7	C1—C6—C7	124.0
N4—C15—H151	109.5	N2—N1—C1	115.6
C16—C15—H151	109.5	N3—N2—N1	172.3
N4—C15—H152	109.5	O2P—C7P—O1P	127 (3)
C16—C15—H152	109.5	O2P—C7P—C6P	127 (3)
H151—C15—H152	108.1	O1P—C7P—C6P	106 (2)
C17—C16—C21	119.1	C2P—C1P—C6P	120.0
C17—C16—C15	120.6	C2P—C1P—N1P	129.5 (17)
C21—C16—C15	120.2	C6P—C1P—N1P	110.0 (17)
C18—C17—C16	120.9	C3P—C2P—C1P	120.0
C18—C17—H17	119.5	C3P—C2P—H2P	120.0
C16—C17—H17	119.5	C1P—C2P—H2P	120.0
C17—C18—C19	119.7	C2P—C3P—C4P	120.0
C17—C18—H18	120.2	C2P—C3P—H3P	120.0
C19—C18—H18	120.2	C4P—C3P—H3P	120.0
C20—C19—C18	119.8	C3P—C4P—C5P	120.0
C20—C19—H19	120.1	C3P—C4P—H4P	120.0
C18—C19—H19	120.1	C5P—C4P—H4P	120.0
C19—C20—C21	120.6	C4P—C5P—C6P	120.0
C19—C20—H20	119.7	C4P—C5P—H5P	120.0
C21—C20—H20	119.7	C6P—C5P—H5P	120.0
C16—C21—C20	119.9	C5P—C6P—C1P	120.0
C16—C21—H21	120.1	C5P—C6P—C7P	134.6 (14)
C20—C21—H21	120.1	C1P—C6P—C7P	105.4 (14)
C8—N4—C15	111.4	O1P—N1P—C1P	104 (2)
C8—N4—H01	108.3	N1P—O1P—C7P	114 (3)

N4—C8—C9—C10	108.7	N1—C1—C6—C5	179.7
N4—C8—C9—C14	−73.2	C2—C1—C6—C7	−178.5
C14—C9—C10—C11	−0.7	N1—C1—C6—C7	2.3
C8—C9—C10—C11	177.5	O1—C7—C6—C5	−140.6
C9—C10—C11—C12	1.1	O2—C7—C6—C5	37.8
C10—C11—C12—C13	0.2	O1—C7—C6—C1	36.8
C11—C12—C13—C14	−1.8	O2—C7—C6—C1	−144.8
C12—C13—C14—C9	2.3	C2—C1—N1—N2	8.9
C10—C9—C14—C13	−1.0	C6—C1—N1—N2	−171.9
C8—C9—C14—C13	−179.1	C1—N1—N2—N3	173.4
N4—C15—C16—C17	−78.2	C6P—C1P—C2P—C3P	0.0
N4—C15—C16—C21	101.8	N1P—C1P—C2P—C3P	−171 (3)
C21—C16—C17—C18	−2.2	C1P—C2P—C3P—C4P	0.0
C15—C16—C17—C18	177.9	C2P—C3P—C4P—C5P	0.0
C16—C17—C18—C19	1.3	C3P—C4P—C5P—C6P	0.0
C17—C18—C19—C20	0.7	C4P—C5P—C6P—C1P	0.0
C18—C19—C20—C21	−1.7	C4P—C5P—C6P—C7P	180 (2)
C17—C16—C21—C20	1.2	C2P—C1P—C6P—C5P	0.0
C15—C16—C21—C20	−178.9	N1P—C1P—C6P—C5P	173 (2)
C19—C20—C21—C16	0.8	C2P—C1P—C6P—C7P	−180.0 (18)
C9—C8—N4—C15	−176.9	N1P—C1P—C6P—C7P	−7 (2)
C16—C15—N4—C8	−172.3	O2P—C7P—C6P—C5P	9 (4)
C6—C1—C2—C3	2.0	O1P—C7P—C6P—C5P	−175.1 (18)
N1—C1—C2—C3	−178.8	O2P—C7P—C6P—C1P	−171 (3)
C1—C2—C3—C4	−1.1	O1P—C7P—C6P—C1P	5 (2)
C2—C3—C4—C5	−0.7	C2P—C1P—N1P—O1P	178.6 (17)
C3—C4—C5—C6	1.7	C6P—C1P—N1P—O1P	7 (3)
C4—C5—C6—C1	−0.8	C1P—N1P—O1P—C7P	−4 (3)
C4—C5—C6—C7	176.8	O2P—C7P—O1P—N1P	175 (3)
C2—C1—C6—C5	−1.1	C6P—C7P—O1P—N1P	−1 (3)

Dibenzylammonium 3-azidebenzoate (3a-db-I-f) top

Crystal data top

C₂₁H₂₀N₄O₂	D_x = 1.235 Mg m⁻³
M_r = 360.41	Melting point: not measured K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.9378 (2) Å	Cell parameters from 8192 reflections
b = 14.5133 (3) Å	µ = 0.08 mm⁻¹
c = 14.9386 (3) Å	T = 80 K
V = 1937.79 (7) Å³	Needle, orange
Z = 4	0.40 × 0.20 × 0.15 mm
F(000) = 760

Data collection top

Bruker SMART CCD area detector system diffractometer	3183 independent reflections
Radiation source: rotating anode	2575 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −12→12
T_min = 0.968, T_max = 0.988	k = −20→20
30720 measured reflections	l = −21→21

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)] = 0.059	H-atom parameters constrained
wR(F²) = 0.181	w = 1/[σ²(F_o²) + (0.1067P)² + 0.5646P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3183 reflections	Δρ_max = 0.35 e Å⁻³
183 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Special details top

Experimental. 'photo-irradiated product 3-nitrenobenzoate is observed

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C8	0.41484 (15)	0.35948 (6)	−0.07201 (7)	0.0319 (5)
H81	0.5211	0.3497	−0.0559	0.038*
H82	0.3725	0.4052	−0.0299	0.038*
C9	0.40572 (11)	0.39691 (6)	−0.16611 (7)	0.0294 (5)
C10	0.51828 (12)	0.37711 (7)	−0.22792 (8)	0.0369 (6)
H10	0.6040	0.3433	−0.2096	0.044*
C11	0.50563 (18)	0.40671 (9)	−0.31642 (8)	0.0480 (8)
H11	0.5815	0.3917	−0.3585	0.058*
C12	0.3824 (2)	0.45806 (9)	−0.34305 (8)	0.0526 (9)
H12	0.3738	0.4781	−0.4034	0.063*
C13	0.27178 (16)	0.48010 (8)	−0.28149 (11)	0.0520 (9)
H13	0.1886	0.5165	−0.2994	0.062*
C14	0.28225 (13)	0.44901 (6)	−0.19330 (10)	0.0403 (7)
H14	0.2053	0.4633	−0.1517	0.048*
C15	0.40374 (9)	0.19026 (6)	−0.10927 (7)	0.0316 (5)
H151	0.5055	0.1805	−0.0849	0.038*
H152	0.4128	0.2036	−0.1740	0.038*
C16	0.31095 (12)	0.10449 (6)	−0.09564 (8)	0.0372 (6)
C17	0.31346 (15)	0.05934 (7)	−0.01311 (9)	0.0426 (7)
H17	0.3755	0.0818	0.0337	0.051*
C18	0.22519 (18)	−0.01860 (7)	0.00075 (11)	0.0581 (10)
H18	0.2272	−0.0492	0.0570	0.070*
C19	0.13409 (18)	−0.05166 (7)	−0.06783 (13)	0.0654 (12)
H19	0.0728	−0.1042	−0.0581	0.078*
C20	0.13296 (19)	−0.00792 (7)	−0.15026 (12)	0.0636 (12)
H20	0.0725	−0.0313	−0.1974	0.076*
C21	0.22067 (15)	0.07061 (6)	−0.16433 (9)	0.0510 (9)
H21	0.2187	0.1009	−0.2207	0.061*
N4	0.33122 (12)	0.27002 (6)	−0.06284 (6)	0.0268 (4)
H01	0.3220	0.2562	−0.0030	0.032*
H02	0.2364	0.2776	−0.0856	0.032*
C7	0.42586 (10)	0.23931 (8)	0.14927 (6)	0.0288 (5)
C1	0.32714 (14)	0.31779 (9)	0.38384 (6)	0.0432 (7)
C2	0.31692 (10)	0.29541 (7)	0.29326 (6)	0.0368 (6)
H2	0.2256	0.3048	0.2620	0.044*
C3	0.44051 (9)	0.25927 (6)	0.24851 (6)	0.0293 (5)
C4	0.57416 (11)	0.24472 (10)	0.29508 (7)	0.0348 (6)
H4	0.6578	0.2183	0.2654	0.042*
C5	0.58436 (14)	0.26907 (13)	0.38539 (7)	0.0449 (7)
H5	0.6759	0.2604	0.4166	0.054*
C6	0.46110 (16)	0.30600 (12)	0.43001 (6)	0.0485 (8)
H6	0.4685	0.3229	0.4913	0.058*
N1	0.20300 (17)	0.35501 (13)	0.43323 (8)	0.0573 (8)
N2	0.08238 (15)	0.35306 (14)	0.39207 (10)	0.0419 (15)	0.75 (2)
N3	−0.03288 (14)	0.35417 (18)	0.36061 (13)	0.0544 (18)	0.75 (2)
O1	0.30008 (11)	0.25634 (10)	0.11408 (6)	0.0364 (4)
O2	0.53725 (12)	0.20796 (9)	0.10780 (7)	0.0349 (4)
N2P	0.054 (5)	0.336 (4)	0.378 (3)	0.152 (10)*	0.25 (2)
N3P	−0.056 (5)	0.368 (3)	0.329 (3)	0.152 (10)*	0.25 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.0309 (12)	0.0273 (11)	0.0375 (13)	−0.0103 (10)	0.0007 (11)	−0.0032 (10)
C9	0.0248 (11)	0.0238 (10)	0.0396 (13)	−0.0059 (9)	−0.0031 (10)	0.0015 (10)
C7	0.0314 (13)	0.0374 (14)	0.0417 (14)	−0.0051 (11)	0.0004 (11)	0.0027 (12)
C11	0.0501 (18)	0.0504 (18)	0.0433 (16)	−0.0130 (15)	0.0080 (14)	0.0039 (14)
C12	0.059 (2)	0.0515 (18)	0.0473 (17)	−0.0243 (17)	−0.0151 (16)	0.0137 (15)
C13	0.0421 (17)	0.0379 (16)	0.076 (2)	−0.0087 (13)	−0.0143 (17)	0.0193 (16)
C14	0.0308 (13)	0.0313 (13)	0.0589 (18)	−0.0002 (11)	0.0006 (13)	0.0064 (13)
C15	0.0250 (11)	0.0290 (12)	0.0408 (13)	0.0003 (10)	0.0009 (11)	0.0010 (10)
C16	0.0249 (11)	0.0268 (11)	0.0599 (17)	0.0012 (10)	0.0004 (12)	−0.0003 (12)
C17	0.0428 (16)	0.0287 (13)	0.0564 (18)	−0.0013 (12)	0.0142 (14)	−0.0024 (12)
C18	0.059 (2)	0.0339 (15)	0.082 (3)	−0.0021 (15)	0.029 (2)	0.0070 (16)
C19	0.0416 (18)	0.0325 (15)	0.122 (4)	−0.0107 (14)	0.015 (2)	−0.002 (2)
C20	0.0364 (16)	0.0380 (16)	0.116 (4)	−0.0042 (14)	−0.019 (2)	0.000 (2)
C21	0.0411 (16)	0.0294 (13)	0.083 (2)	−0.0013 (12)	−0.0210 (17)	0.0042 (15)
N4	0.0205 (9)	0.0248 (9)	0.0351 (10)	−0.0040 (7)	−0.0018 (8)	0.0017 (8)
C7	0.0228 (10)	0.0315 (12)	0.0321 (11)	−0.0018 (9)	0.0014 (9)	0.0044 (10)
C1	0.0480 (17)	0.0440 (16)	0.0377 (14)	−0.0045 (14)	0.0078 (14)	0.0030 (13)
C2	0.0342 (13)	0.0401 (14)	0.0362 (13)	−0.0023 (12)	0.0049 (11)	0.0035 (11)
C3	0.0272 (11)	0.0295 (11)	0.0310 (11)	−0.0053 (9)	0.0015 (9)	0.0047 (10)
C4	0.0288 (12)	0.0358 (13)	0.0399 (13)	−0.0049 (11)	−0.0016 (11)	0.0088 (11)
C5	0.0445 (16)	0.0487 (17)	0.0414 (14)	−0.0145 (14)	−0.0099 (13)	0.0124 (13)
C6	0.064 (2)	0.0498 (18)	0.0322 (13)	−0.0130 (17)	0.0002 (14)	0.0023 (13)
N1	0.0608 (19)	0.071 (2)	0.0398 (14)	−0.0012 (17)	0.0144 (14)	−0.0042 (14)
N2	0.038 (2)	0.051 (2)	0.037 (2)	−0.0071 (16)	0.0156 (16)	−0.0142 (16)
N3	0.028 (2)	0.074 (3)	0.061 (3)	0.0027 (19)	0.0145 (19)	−0.027 (2)
O1	0.0216 (8)	0.0511 (12)	0.0366 (9)	0.0037 (8)	0.0005 (7)	0.0044 (9)
O2	0.0221 (8)	0.0424 (11)	0.0401 (10)	0.0020 (8)	0.0031 (8)	−0.0016 (9)

Geometric parameters (Å, º) top

C8—N4	1.5043	C19—C20	1.3854
C8—C9	1.5093	C19—H19	0.9500
C8—H81	0.9900	C20—C21	1.3991
C8—H82	0.9900	C20—H20	0.9500
C9—C10	1.3955	C21—H21	0.9500
C9—C14	1.3980	N4—H01	0.9200
C10—C11	1.3947	N4—H02	0.9200
C10—H10	0.9500	C7—O2	1.2578
C11—C12	1.3880	C7—O1	1.2654
C11—H11	0.9500	C7—C3	1.5162
C12—C13	1.3877	C1—C6	1.3923
C12—H12	0.9500	C1—C2	1.3945
C13—C14	1.3957	C1—N1	1.4378
C13—H13	0.9500	C2—C3	1.3937
C14—H14	0.9500	C2—H2	0.9500
C15—N4	1.4971	C3—C4	1.3983
C15—C16	1.5095	C4—C5	1.3976
C15—H151	0.9900	C4—H4	0.9500
C15—H152	0.9900	C5—C6	1.3947
C16—C21	1.3949	C5—H5	0.9500
C16—C17	1.3964	C6—H6	0.9500
C17—C18	1.3946	N1—N2	1.2415
C17—H17	0.9500	N1—N1ⁱ	5.766 (3)
C18—C19	1.3938	N2—N3	1.1324
C18—H18	0.9500	N2P—N3P	1.32 (5)

N4—C8—C9	111.6	C20—C19—H19	120.0
N4—C8—H81	109.3	C18—C19—H19	120.0
C9—C8—H81	109.3	C19—C20—C21	120.2
N4—C8—H82	109.3	C19—C20—H20	119.9
C9—C8—H82	109.3	C21—C20—H20	119.9
H81—C8—H82	108.0	C16—C21—C20	120.0
C10—C9—C14	119.2	C16—C21—H21	120.0
C10—C9—C8	120.2	C20—C21—H21	120.0
C14—C9—C8	120.5	C15—N4—C8	114.2
C11—C10—C9	120.4	C15—N4—H01	108.7
C11—C10—H10	119.8	C8—N4—H01	108.7
C9—C10—H10	119.8	C15—N4—H02	108.7
C12—C11—C10	120.1	C8—N4—H02	108.7
C12—C11—H11	120.0	H01—N4—H02	107.6
C10—C11—H11	120.0	O2—C7—O1	124.7
C13—C12—C11	120.0	O2—C7—C3	118.8
C13—C12—H12	120.0	O1—C7—C3	116.5
C11—C12—H12	120.0	C6—C1—C2	120.6
C12—C13—C14	120.2	C6—C1—N1	117.1
C12—C13—H13	119.9	C2—C1—N1	122.3
C14—C13—H13	119.9	C3—C2—C1	120.1
C13—C14—C9	120.1	C3—C2—H21	120.0
C13—C14—H14	119.9	C1—C2—H21	120.0
C9—C14—H14	119.9	C2—C3—C4	119.7
N4—C15—C16	109.7	C2—C3—C7	118.2
N4—C15—H151	109.7	C4—C3—C7	122.1
C16—C15—H151	109.7	C5—C4—C3	119.9
N4—C15—H152	109.7	C5—C4—H14	120.1
C16—C15—H152	109.7	C3—C4—H14	120.1
H151—C15—H152	108.2	C6—C5—C4	120.5
C21—C16—C17	119.6	C6—C5—H151	119.8
C21—C16—C15	120.6	C4—C5—H152	119.8
C17—C16—C15	119.8	C1—C6—C5	119.3
C18—C17—C16	120.2	C1—C6—H6	120.3
C18—C17—H17	119.9	C5—C6—H6	120.3
C16—C17—H17	119.9	N2—N1—C1	114.0
C19—C18—C17	120.0	N2—N1—N1ⁱ	146.35 (6)
C19—C18—H18	120.0	C1—N1—N1ⁱ	51.7
C17—C18—H18	120.0	N3—N2—N1	174.4
C20—C19—C18	120.0

N4—C8—C9—C10	−93.9	C9—C8—N4—C15	70.6
N4—C8—C9—C14	83.8	C6—C1—C2—C3	1.2
C14—C9—C10—C11	−1.8	N1—C1—C2—C3	−179.8
C8—C9—C10—C11	176.0	C1—C2—C3—C4	0.6
C9—C10—C11—C12	1.6	C1—C2—C3—C7	−177.8
C10—C11—C12—C13	0.1	O2—C7—C3—C2	179.0
C11—C12—C13—C14	−1.5	O1—C7—C3—C2	−0.7
C12—C13—C14—C9	1.2	O2—C7—C3—C4	0.6
C10—C9—C14—C13	0.5	O1—C7—C3—C4	−179.1
C8—C9—C14—C13	−177.3	C2—C3—C4—C5	−1.9
N4—C15—C16—C21	103.6	C7—C3—C4—C5	176.4
N4—C15—C16—C17	−75.3	C3—C4—C5—C6	1.4
C21—C16—C17—C18	−0.6	C2—C1—C6—C5	−1.8
C15—C16—C17—C18	178.4	N1—C1—C6—C5	179.2
C16—C17—C18—C19	0.0	C4—C5—C6—C1	0.5
C17—C18—C19—C20	1.0	C6—C1—N1—N2	−171.4
C18—C19—C20—C21	−1.4	C2—C1—N1—N2	9.7
C17—C16—C21—C20	0.2	C6—C1—N1—N1ⁱ	−27.36 (7)
C15—C16—C21—C20	−178.7	C2—C1—N1—N1ⁱ	153.66 (7)
C19—C20—C21—C16	0.8	C1—N1—N2—N3	177 (100)
C16—C15—N4—C8	179.9	N1ⁱ—N1—N2—N3	120.9

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

Dibenzylammonium 3-azidebenzoate (3a-db-II-f) top

Crystal data top

C₂₁H₂₀N₄O₂	F(000) = 760
M_r = 360.41	D_x = 1.216 Mg m⁻³
Monoclinic, P2₁/c	Melting point: not measured K
a = 10.908 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7884 (18) Å	Cell parameters from 7397 reflections
c = 21.240 (4) Å	µ = 0.08 mm⁻¹
β = 104.87 (3)°	T = 82 K
V = 1967.9 (7) Å³	Needle, pale-yellow
Z = 4	0.31 × 0.16 × 0.12 mm

Data collection top

Bruker SMART CCD area detector system diffractometer	5734 independent reflections
Radiation source: rotating anode	4338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −15→15
T_min = 0.975, T_max = 0.990	k = −12→12
30460 measured reflections	l = −29→29

Refinement top

Refinement on F²	Primary atom site location: rigid model
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0911P)² + 1.2767P] where P = (F_o² + 2F_c²)/3
5734 reflections	(Δ/σ)_max < 0.001
206 parameters	Δρ_max = 0.57 e Å⁻³
5 restraints	Δρ_min = −0.56 e Å⁻³

Special details top

Experimental. 'photo-irradiated product 3,3'-dicarboxy-trans-azobenzene is observed'

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C8	0.17213 (6)	0.71400 (9)	0.25544 (3)	0.0255 (3)
H81	0.2005	0.6865	0.3021	0.031*
H82	0.1319	0.8156	0.2524	0.031*
C9	0.28668 (5)	0.72342 (7)	0.22800 (3)	0.0240 (3)
C10	0.28565 (5)	0.81927 (7)	0.17506 (4)	0.0288 (4)
H10	0.2124	0.8782	0.1563	0.035*
C11	0.39182 (6)	0.82857 (10)	0.14979 (4)	0.0340 (4)
H11	0.3902	0.8929	0.1137	0.041*
C12	0.49992 (5)	0.74350 (11)	0.17758 (4)	0.0359 (4)
H12	0.5721	0.7502	0.1605	0.043*
C13	0.50215 (4)	0.64844 (9)	0.23055 (5)	0.0341 (4)
H13	0.5759	0.5906	0.2495	0.041*
C14	0.39578 (5)	0.63839 (8)	0.25569 (4)	0.0290 (4)
H14	0.3976	0.5736	0.2917	0.035*
C15	0.00796 (4)	0.64688 (6)	0.15304 (3)	0.0282 (4)
H151	0.0698	0.6494	0.1261	0.034*
H152	−0.0263	0.7509	0.1539	0.034*
C16	−0.09913 (5)	0.53988 (7)	0.12219 (3)	0.0280 (4)
C17	−0.08863 (6)	0.44197 (9)	0.07192 (3)	0.0372 (4)
H17	−0.0130	0.4413	0.0576	0.045*
C18	−0.18871 (7)	0.34511 (11)	0.04265 (4)	0.0473 (6)
H18	−0.1810	0.2790	0.0085	0.057*
C19	−0.29958 (6)	0.34555 (10)	0.06360 (5)	0.0484 (6)
H19	−0.3677	0.2799	0.0437	0.058*
C20	−0.31059 (5)	0.44258 (10)	0.11390 (5)	0.0418 (5)
H20	−0.3862	0.4424	0.1283	0.050*
C21	−0.21104 (5)	0.53981 (9)	0.14314 (4)	0.0323 (4)
H21	−0.2191	0.6059	0.1772	0.039*
N4	0.07458 (5)	0.59982 (8)	0.22107 (3)	0.0236 (3)
H02	0.1138	0.5077	0.2196	0.028*
H01	0.0155	0.5868	0.2447	0.028*
C1	0.19678 (6)	0.16036 (7)	0.02177 (3)	0.0267 (4)	0.923 (4)
C2	0.14210 (6)	0.13520 (7)	0.07353 (3)	0.0225 (4)	0.923 (4)
H2	0.0798	0.0581	0.0705	0.027*	0.923 (4)
C3	0.17957 (6)	0.22403 (6)	0.12982 (3)	0.0196 (3)	0.923 (4)
C4	0.27046 (8)	0.33869 (9)	0.13361 (3)	0.0244 (4)	0.923 (4)
H4	0.2962	0.3991	0.1718	0.029*	0.923 (4)
C5	0.32313 (9)	0.36409 (10)	0.08115 (4)	0.0284 (4)	0.923 (4)
H5	0.3840	0.4428	0.0837	0.034*	0.923 (4)
C6	0.28742 (8)	0.27513 (9)	0.02492 (3)	0.0309 (4)	0.923 (4)
H6	0.3239	0.2921	−0.0106	0.037*	0.923 (4)
C7	0.12082 (7)	0.19626 (8)	0.18627 (3)	0.0212 (4)	0.923 (4)
O1	0.13741 (9)	0.29562 (10)	0.23092 (3)	0.0260 (3)	0.923 (4)
O2	0.05916 (10)	0.07375 (10)	0.18578 (4)	0.0259 (3)	0.923 (4)
N1	0.15157 (9)	0.06391 (10)	−0.03395 (3)	0.0389 (5)	0.923 (4)
N2	0.21439 (10)	0.06437 (11)	−0.07524 (3)	0.0322 (5)	0.823 (4)
N3	0.26331 (12)	0.05379 (13)	−0.11617 (4)	0.0431 (6)	0.823 (4)
C1P	0.118 (2)	0.148 (3)	0.0376 (9)	0.056 (4)*	0.075 (4)
C2P	0.099 (2)	0.126 (2)	0.0992 (10)	0.056 (4)*	0.075 (4)
H2P	0.0387	0.0529	0.1054	0.067*	0.075 (4)
C3P	0.167 (2)	0.212 (3)	0.1516 (9)	0.056 (4)*	0.075 (4)
C4P	0.254 (2)	0.319 (3)	0.1426 (10)	0.056 (4)*	0.075 (4)
H4P	0.3008	0.3773	0.1784	0.067*	0.075 (4)
C5P	0.274 (2)	0.341 (3)	0.0810 (12)	0.056 (4)*	0.075 (4)
H5P	0.3333	0.4142	0.0748	0.067*	0.075 (4)
C6P	0.205 (2)	0.255 (3)	0.0286 (9)	0.056 (4)*	0.075 (4)
H6P	0.2186	0.2705	−0.0135	0.067*	0.075 (4)
C7P	0.134 (2)	0.201 (3)	0.209 (2)	0.056 (4)*	0.075 (4)
O1P	0.159 (3)	0.318 (4)	0.2516 (15)	0.056 (4)*	0.075 (4)
O2P	0.073 (3)	0.073 (3)	0.2096 (15)	0.056 (4)*	0.075 (4)
N1P	0.037 (3)	0.049 (4)	−0.0078 (17)	0.066 (9)*	0.075 (4)
N2P	0.395 (3)	0.032 (4)	−0.0624 (15)	0.136 (10)*	0.177 (4)
N3P	0.477 (2)	0.019 (3)	−0.0176 (11)	0.106 (7)*	0.177 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.0274 (8)	0.0198 (7)	0.0315 (8)	−0.0031 (6)	0.0117 (6)	−0.0039 (6)
C9	0.0242 (7)	0.0181 (7)	0.0309 (8)	−0.0033 (6)	0.0090 (6)	−0.0043 (6)
C10	0.0271 (8)	0.0213 (7)	0.0399 (9)	−0.0001 (6)	0.0122 (7)	0.0022 (7)
C11	0.0339 (9)	0.0285 (8)	0.0438 (10)	−0.0038 (7)	0.0175 (8)	0.0043 (8)
C12	0.0262 (8)	0.0340 (9)	0.0515 (11)	−0.0060 (7)	0.0173 (8)	−0.0034 (8)
C13	0.0224 (8)	0.0334 (9)	0.0452 (11)	−0.0003 (7)	0.0064 (7)	−0.0027 (8)
C14	0.0270 (8)	0.0265 (8)	0.0327 (9)	−0.0023 (6)	0.0062 (7)	−0.0010 (7)
C15	0.0246 (8)	0.0275 (8)	0.0321 (8)	−0.0016 (6)	0.0064 (6)	0.0050 (7)
C16	0.0248 (8)	0.0254 (8)	0.0317 (8)	0.0026 (6)	0.0033 (6)	0.0044 (6)
C17	0.0333 (9)	0.0365 (10)	0.0384 (10)	0.0084 (8)	0.0030 (8)	0.0013 (8)
C18	0.0525 (13)	0.0334 (10)	0.0461 (12)	0.0078 (9)	−0.0053 (10)	−0.0072 (9)
C19	0.0407 (11)	0.0358 (11)	0.0555 (13)	−0.0088 (9)	−0.0114 (10)	0.0046 (10)
C20	0.0297 (9)	0.0423 (11)	0.0487 (12)	−0.0056 (8)	0.0014 (8)	0.0099 (9)
C21	0.0269 (8)	0.0326 (9)	0.0353 (9)	−0.0003 (7)	0.0043 (7)	0.0048 (7)
N4	0.0228 (6)	0.0188 (6)	0.0315 (7)	−0.0003 (5)	0.0113 (5)	0.0007 (5)
C1	0.0284 (9)	0.0272 (9)	0.0252 (8)	−0.0026 (7)	0.0082 (7)	−0.0026 (7)
C2	0.0238 (8)	0.0207 (7)	0.0252 (8)	−0.0023 (6)	0.0102 (7)	0.0001 (6)
C3	0.0189 (7)	0.0176 (7)	0.0233 (8)	0.0019 (6)	0.0073 (6)	0.0023 (6)
C4	0.0236 (8)	0.0221 (8)	0.0270 (9)	−0.0036 (6)	0.0057 (7)	−0.0019 (7)
C5	0.0213 (8)	0.0305 (9)	0.0331 (9)	−0.0073 (7)	0.0064 (7)	0.0029 (7)
C6	0.0294 (9)	0.0376 (10)	0.0276 (9)	−0.0038 (8)	0.0106 (7)	0.0028 (8)
C7	0.0223 (8)	0.0190 (7)	0.0240 (8)	0.0046 (6)	0.0089 (6)	0.0010 (6)
O1	0.0344 (8)	0.0198 (6)	0.0258 (7)	0.0019 (5)	0.0113 (6)	−0.0030 (5)
O2	0.0332 (7)	0.0200 (6)	0.0292 (7)	−0.0014 (5)	0.0165 (6)	−0.0023 (6)
N1	0.0454 (11)	0.0437 (11)	0.0318 (9)	−0.0146 (8)	0.0175 (8)	−0.0099 (8)
N2	0.0435 (11)	0.0260 (9)	0.0307 (9)	−0.0050 (8)	0.0157 (8)	−0.0027 (7)
N3	0.0656 (15)	0.0348 (11)	0.0390 (12)	−0.0099 (10)	0.0317 (11)	−0.0074 (9)

Geometric parameters (Å, º) top

C8—N4	1.5077	C1—C6	1.4020
C8—C9	1.5104	C1—N1	1.4362
C8—H81	0.9900	C2—C3	1.3983
C8—H82	0.9900	C2—H2	0.9500
C9—C14	1.4005	C3—C4	1.4013
C9—C10	1.4027	C3—C7	1.5173
C10—C11	1.3981	C4—C5	1.3964
C10—H10	0.9500	C4—H4	0.9500
C11—C12	1.3930	C5—C6	1.3967
C11—H11	0.9500	C5—H5	0.9500
C12—C13	1.3966	C6—H6	0.9500
C12—H12	0.9500	C7—O1	1.2674
C13—C14	1.3989	C7—O2	1.2681
C13—H13	0.9500	N1—N2	1.2438
C14—H14	0.9500	N2—N3	1.1346
C15—N4	1.4994	C1P—C2P	1.3900
C15—C16	1.5117	C1P—C6P	1.3900
C15—H151	0.9900	C1P—N1P	1.42 (4)
C15—H152	0.9900	C2P—C3P	1.3900
C16—C17	1.3987	C2P—H2P	0.9500
C16—C21	1.4024	C3P—C7P	1.35 (5)
C17—C18	1.3980	C3P—C4P	1.3900
C17—H17	0.9500	C4P—C5P	1.3900
C18—C19	1.3916	C4P—H4P	0.9500
C18—H18	0.9500	C5P—C6P	1.3900
C19—C20	1.3959	C5P—H5P	0.9500
C19—H19	0.9500	C6P—H6P	0.9500
C20—C21	1.3960	C7P—O2P	1.308 (19)
C20—H20	0.9500	C7P—O1P	1.35 (4)
C21—H36	0.9500	N1P—N1Pⁱ	1.29 (7)
N4—H02	0.9200	N2P—N3P	1.13 (3)
N4—H01	0.9200	N3P—N3Pⁱⁱ	0.85 (4)
C1—C2	1.3962

N4—C8—C9	113.6	C8—N4—H02	109.0
N4—C8—H81	108.8	C15—N4—H01	109.0
C9—C8—H81	108.8	C8—N4—H01	109.0
N4—C8—H82	108.8	H02—N4—H01	107.8
C9—C8—H82	108.8	C2—C1—C6	121.0
H81—C8—H82	107.7	C2—C1—N1	115.4
C14—C9—C10	119.2	C6—C1—N1	123.5
C14—C9—C8	120.4	C1—C2—C3	119.6
C10—C9—C8	120.3	C1—C2—H2	120.2
C11—C10—C9	120.4	C3—C2—H2	120.2
C11—C10—H10	119.8	C2—C3—C4	119.9
C9—C10—H10	119.8	C2—C3—C7	119.7
C12—C11—C10	120.0	C4—C3—C7	120.4
C12—C11—H11	120.0	C5—C4—C3	119.9
C10—C11—H11	120.0	C5—C4—H4	120.0
C11—C12—C13	120.0	C3—C4—H4	120.0
C11—C12—H12	120.0	C4—C5—C6	120.7
C13—C12—H12	120.0	C4—C5—H5	119.6
C12—C13—C14	120.0	C6—C5—H5	119.6
C12—C13—H13	120.0	C5—C6—C1	118.8
C14—C13—H13	120.0	C5—C6—H6	120.6
C13—C14—C9	120.3	C1—C6—H6	120.6
C13—C14—H14	119.8	O1—C7—O2	124.4
C9—C14—H14	119.8	O1—C7—C3	118.2
N4—C15—C16	112.1	O2—C7—C3	117.4
N4—C15—H151	109.2	N2—N1—C1	116.4
C16—C15—H151	109.2	N3—N2—N1	173.0
N4—C15—H152	109.2	C2P—C1P—C6P	120.0
C16—C15—H152	109.2	C2P—C1P—N1P	110 (2)
H151—C15—H152	107.9	C6P—C1P—N1P	130 (2)
C17—C16—C21	119.4	C1P—C2P—C3P	120.0
C17—C16—C15	120.5	C1P—C2P—H2P	120.0
C21—C16—C15	120.1	C3P—C2P—H2P	120.0
C18—C17—C16	120.4	C7P—C3P—C4P	121.2 (8)
C18—C17—H17	119.8	C7P—C3P—C2P	118.3 (8)
C16—C17—H17	119.8	C4P—C3P—C2P	120.0
C19—C18—C17	120.0	C3P—C4P—C5P	120.0
C19—C18—H18	120.0	C3P—C4P—H4P	120.0
C17—C18—H18	120.0	C5P—C4P—H4P	120.0
C18—C19—C20	119.9	C6P—C5P—C4P	120.0
C18—C19—H19	120.0	C6P—C5P—H5P	120.0
C20—C19—H19	120.0	C4P—C5P—H5P	120.0
C19—C20—C21	120.3	C5P—C6P—C1P	120.0
C19—C20—H20	119.9	C5P—C6P—H6P	120.0
C21—C20—H20	119.9	C1P—C6P—H6P	120.0
C20—C21—C16	120.0	O2P—C7P—O1P	131 (4)
C20—C21—H36	120.0	O2P—C7P—C3P	109 (3)
C16—C21—H36	120.0	O1P—C7P—C3P	120 (2)
C15—N4—C8	113.0	N1Pⁱ—N1P—C1P	124 (4)
C15—N4—H02	109.0	N3Pⁱⁱ—N3P—N2P	158 (5)

N4—C8—C9—C14	−94.6	C3—C4—C5—C6	−0.8
N4—C8—C9—C10	86.4	C4—C5—C6—C1	0.5
C14—C9—C10—C11	0.7	C2—C1—C6—C5	0.4
C8—C9—C10—C11	179.7	N1—C1—C6—C5	178.9
C9—C10—C11—C12	−0.6	C2—C3—C7—O1	−166.6
C10—C11—C12—C13	0.2	C4—C3—C7—O1	13.0
C11—C12—C13—C14	0.1	C2—C3—C7—O2	14.1
C12—C13—C14—C9	0.0	C4—C3—C7—O2	−166.3
C10—C9—C14—C13	−0.3	C2—C1—N1—N2	−167.1
C8—C9—C14—C13	−179.4	C6—C1—N1—N2	14.2
N4—C15—C16—C17	−109.1	C1—N1—N2—N3	177.1
N4—C15—C16—C21	72.0	C6P—C1P—C2P—C3P	0.0
C21—C16—C17—C18	0.2	N1P—C1P—C2P—C3P	−180 (3)
C15—C16—C17—C18	−178.8	C1P—C2P—C3P—C7P	171.9 (19)
C16—C17—C18—C19	−0.1	C1P—C2P—C3P—C4P	0.0
C17—C18—C19—C20	−0.1	C7P—C3P—C4P—C5P	−171.6 (19)
C18—C19—C20—C21	0.3	C2P—C3P—C4P—C5P	0.0
C19—C20—C21—C16	−0.3	C3P—C4P—C5P—C6P	0.0
C17—C16—C21—C20	0.0	C4P—C5P—C6P—C1P	0.0
C15—C16—C21—C20	179.0	C2P—C1P—C6P—C5P	0.0
C16—C15—N4—C8	−173.7	N1P—C1P—C6P—C5P	179 (3)
C9—C8—N4—C15	−69.2	C4P—C3P—C7P—O2P	−166.7 (19)
C6—C1—C2—C3	−1.0	C2P—C3P—C7P—O2P	22 (2)
N1—C1—C2—C3	−179.7	C4P—C3P—C7P—O1P	18 (2)
C1—C2—C3—C4	0.8	C2P—C3P—C7P—O1P	−154 (2)
C1—C2—C3—C7	−179.7	C2P—C1P—N1P—N1Pⁱ	−3 (6)
C2—C3—C4—C5	0.1	C6P—C1P—N1P—N1Pⁱ	178 (4)
C7—C3—C4—C5	−179.5

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

Dicyclohexylammonium 3-azidebenzoate (3a-dc-f) top

Crystal data top

C₁₉H₂₈N₄O₂	Z = 2
M_r = 344.45	F(000) = 372
Triclinic, P1	D_x = 1.244 Mg m⁻³
a = 9.2356 (4) Å	Melting point: not measured K
b = 10.2844 (5) Å	Mo Kα radiation, λ = 0.71073 Å
c = 11.3770 (6) Å	µ = 0.08 mm⁻¹
α = 111.073 (2)°	T = 82 K
β = 103.254 (2)°	Plate, pale-yellow
γ = 103.553 (2)°	0.44 × 0.38 × 0.26 mm
V = 919.86 (8) Å³

Data collection top

Bruker SMART CCD area detector system diffractometer	5328 independent reflections
Radiation source: rotating anode	4342 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −12→12
T_min = 0.965, T_max = 0.979	k = −14→14
14760 measured reflections	l = −16→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ²(F_o²) + (0.0866P)² + 0.4358P] where P = (F_o² + 2F_c²)/3
5328 reflections	(Δ/σ)_max < 0.001
171 parameters	Δρ_max = 0.40 e Å⁻³
1 restraint	Δρ_min = −0.46 e Å⁻³

Special details top

Experimental. 'photo-irradiated product 2,1-benzisoxazolone is observed

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C8	0.19633 (4)	0.33724 (4)	0.51373 (3)	0.01734 (19)
H8	0.1506	0.2261	0.4688	0.021*
C9	0.37804 (4)	0.38581 (6)	0.56381 (3)	0.0201 (2)
H91	0.4247	0.4953	0.6004	0.024*
H92	0.4134	0.3410	0.4878	0.024*
C10	0.43674 (6)	0.33697 (7)	0.67355 (4)	0.0220 (2)
H101	0.3977	0.2270	0.6346	0.026*
H102	0.5542	0.3728	0.7072	0.026*
C11	0.37833 (6)	0.39870 (7)	0.79071 (4)	0.0269 (2)
H111	0.4236	0.5087	0.8341	0.032*
H112	0.4147	0.3633	0.8585	0.032*
C12	0.19581 (6)	0.34746 (7)	0.73954 (4)	0.0267 (2)
H121	0.1510	0.2379	0.7031	0.032*
H122	0.1596	0.3911	0.8153	0.032*
C13	0.13471 (6)	0.39488 (7)	0.62957 (4)	0.0214 (2)
H131	0.0172	0.3555	0.5947	0.026*
H132	0.1699	0.5047	0.6686	0.026*
C14	0.18605 (4)	0.35496 (4)	0.29121 (3)	0.01696 (19)
H14	0.3027	0.4082	0.3205	0.020*
C15	0.09899 (6)	0.41111 (5)	0.19818 (4)	0.0194 (2)
H151	0.1259	0.5198	0.2471	0.023*
H152	−0.0171	0.3630	0.1716	0.023*
C16	0.14561 (7)	0.37646 (6)	0.07154 (4)	0.0214 (2)
H161	0.0807	0.4052	0.0098	0.026*
H162	0.2584	0.4364	0.0973	0.026*
C17	0.12131 (7)	0.21073 (6)	−0.00159 (3)	0.0242 (2)
H171	0.1632	0.1947	−0.0764	0.029*
H172	0.0064	0.1517	−0.0401	0.029*
C18	0.20644 (8)	0.15734 (6)	0.09495 (4)	0.0241 (2)
H181	0.3225	0.2090	0.1259	0.029*
H182	0.1842	0.0493	0.0467	0.029*
C19	0.15208 (6)	0.18773 (4)	0.21741 (3)	0.0205 (2)
H191	0.0371	0.1324	0.1877	0.025*
H192	0.2097	0.1538	0.2785	0.025*
N4	0.13726 (5)	0.39508 (5)	0.41397 (3)	0.01682 (17)
H01	0.0281	0.3610	0.3854	0.020*
H02	0.1716	0.4971	0.4586	0.020*
C7	0.70870 (5)	0.21398 (4)	0.35477 (4)	0.0208 (2)
C1	0.33130 (5)	−0.12219 (4)	0.23526 (5)	0.0268 (2)
C2	0.45416 (4)	0.01587 (4)	0.31703 (4)	0.0226 (2)
H2	0.4558	0.0763	0.4035	0.027*
C3	0.57452 (4)	0.06359 (4)	0.26956 (4)	0.0214 (2)
C4	0.57107 (6)	−0.02645 (5)	0.14191 (4)	0.0283 (2)
H4	0.6532	0.0050	0.1104	0.034*
C5	0.44676 (7)	−0.16284 (6)	0.06067 (5)	0.0332 (3)
H5	0.4440	−0.2227	−0.0264	0.040*
C6	0.32710 (6)	−0.21101 (5)	0.10724 (5)	0.0321 (3)
H6	0.2432	−0.3036	0.0523	0.038*
O1	0.69944 (6)	0.29962 (5)	0.46306 (5)	0.02617 (19)
O2	0.81857 (5)	0.24170 (6)	0.30853 (5)	0.02648 (19)
N1	0.20316 (6)	−0.18301 (6)	0.27312 (6)	0.0354 (3)
N2	0.19491 (6)	−0.10253 (7)	0.38192 (7)	0.0244 (3)	0.817 (4)
N3	0.17079 (8)	−0.04254 (9)	0.47701 (8)	0.0328 (4)	0.817 (4)
N2P	0.159 (2)	−0.0365 (19)	0.4832 (17)	0.092 (4)*	0.183 (4)
N3P	0.1175 (18)	−0.0435 (17)	0.5514 (15)	0.092 (4)*	0.183 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.0159 (4)	0.0218 (5)	0.0144 (4)	0.0063 (4)	0.0058 (3)	0.0080 (4)
C9	0.0165 (4)	0.0248 (5)	0.0192 (5)	0.0066 (4)	0.0062 (4)	0.0101 (4)
C10	0.0184 (5)	0.0264 (5)	0.0200 (5)	0.0075 (4)	0.0044 (4)	0.0104 (4)
C11	0.0269 (5)	0.0350 (6)	0.0174 (5)	0.0113 (5)	0.0052 (4)	0.0112 (5)
C12	0.0272 (6)	0.0397 (6)	0.0201 (5)	0.0143 (5)	0.0116 (4)	0.0165 (5)
C13	0.0200 (5)	0.0298 (5)	0.0174 (5)	0.0104 (4)	0.0093 (4)	0.0107 (4)
C14	0.0164 (4)	0.0204 (4)	0.0139 (4)	0.0060 (4)	0.0070 (3)	0.0065 (4)
C15	0.0210 (5)	0.0220 (5)	0.0166 (4)	0.0084 (4)	0.0073 (4)	0.0087 (4)
C16	0.0244 (5)	0.0237 (5)	0.0166 (5)	0.0074 (4)	0.0085 (4)	0.0091 (4)
C17	0.0314 (6)	0.0244 (5)	0.0153 (5)	0.0085 (4)	0.0097 (4)	0.0070 (4)
C18	0.0316 (6)	0.0239 (5)	0.0202 (5)	0.0127 (4)	0.0135 (4)	0.0085 (4)
C19	0.0249 (5)	0.0216 (5)	0.0171 (4)	0.0098 (4)	0.0098 (4)	0.0082 (4)
N4	0.0155 (4)	0.0202 (4)	0.0140 (4)	0.0061 (3)	0.0057 (3)	0.0064 (3)
C7	0.0167 (4)	0.0210 (5)	0.0215 (5)	0.0055 (4)	0.0050 (4)	0.0075 (4)
C1	0.0205 (5)	0.0272 (5)	0.0332 (6)	0.0076 (4)	0.0061 (4)	0.0159 (5)
C2	0.0199 (5)	0.0226 (5)	0.0240 (5)	0.0075 (4)	0.0060 (4)	0.0098 (4)
C3	0.0177 (5)	0.0205 (5)	0.0227 (5)	0.0066 (4)	0.0047 (4)	0.0074 (4)
C4	0.0256 (5)	0.0257 (5)	0.0268 (6)	0.0060 (4)	0.0099 (5)	0.0057 (5)
C5	0.0341 (6)	0.0252 (6)	0.0277 (6)	0.0063 (5)	0.0077 (5)	0.0024 (5)
C6	0.0257 (6)	0.0243 (5)	0.0369 (7)	0.0042 (5)	0.0015 (5)	0.0119 (5)
O1	0.0246 (4)	0.0224 (4)	0.0249 (4)	0.0054 (3)	0.0095 (3)	0.0044 (3)
O2	0.0181 (4)	0.0294 (4)	0.0255 (4)	0.0037 (3)	0.0079 (3)	0.0077 (3)
N1	0.0304 (6)	0.0309 (6)	0.0361 (6)	0.0013 (4)	0.0077 (5)	0.0135 (5)
N2	0.0192 (6)	0.0221 (6)	0.0292 (7)	0.0035 (4)	0.0060 (5)	0.0122 (5)
N3	0.0282 (7)	0.0289 (7)	0.0377 (8)	0.0058 (5)	0.0119 (6)	0.0131 (6)

Geometric parameters (Å, º) top

C8—N4	1.5143	C17—C18	1.5382
C8—C13	1.5337	C17—H171	0.9900
C8—C9	1.5344	C17—H172	0.9900
C8—H8	1.0000	C18—C19	1.5401
C9—C10	1.5406	C18—H181	0.9900
C9—H91	0.9900	C18—H182	0.9900
C9—H92	0.9900	C19—H191	0.9900
C10—C11	1.5337	C19—H192	0.9900
C10—H101	0.9900	N4—H01	0.9200
C10—H102	0.9900	N4—H02	0.9200
C11—C12	1.5399	C7—O1	1.2665
C11—H111	0.9900	C7—O2	1.2668
C11—H112	0.9900	C7—C3	1.5298
C12—C13	1.5382	C1—C6	1.3993
C12—H121	0.9900	C1—C2	1.4071
C12—H122	0.9900	C1—N1	1.4346
C13—H131	0.9900	C2—C3	1.4065
C13—H132	0.9900	C2—H2	0.9500
C14—N4	1.5116	C3—C4	1.4019
C14—C19	1.5327	C4—C5	1.4023
C14—C15	1.5386	C4—H4	0.9500
C14—H14	1.0000	C5—C6	1.3957
C15—C16	1.5412	C5—H5	0.9500
C15—H151	0.9900	C6—H6	0.9500
C15—H152	0.9900	N1—N2	1.2486
C16—C17	1.5371	N1—N1ⁱ	5.8529 (11)
C16—H161	0.9900	N2—N3	1.1382
C16—H162	0.9900	N2P—N3P	0.959 (14)

N4—C8—C13	107.6	C15—C16—H162	109.2
N4—C8—C9	111.3	H161—C16—H162	107.9
C13—C8—C9	111.6	C16—C17—C18	111.0
N4—C8—H8	108.8	C16—C17—H171	109.4
C13—C8—H8	108.8	C18—C17—H171	109.4
C9—C8—H8	108.8	C16—C17—H172	109.4
C8—C9—C10	110.6	C18—C17—H172	109.4
C8—C9—H91	109.5	H171—C17—H172	108.0
C10—C9—H91	109.5	C17—C18—C19	111.5
C8—C9—H92	109.5	C17—C18—H181	109.3
C10—C9—H92	109.5	C19—C18—H181	109.3
H91—C9—H92	108.1	C17—C18—H182	109.3
C11—C10—C9	111.2	C19—C18—H182	109.3
C11—C10—H101	109.4	H181—C18—H182	108.0
C9—C10—H101	109.4	C14—C19—C18	109.0
C11—C10—H102	109.4	C14—C19—H191	109.9
C9—C10—H102	109.4	C18—C19—H191	109.9
H101—C10—H102	108.0	C14—C19—H192	109.9
C10—C11—C12	110.1	C18—C19—H192	109.9
C10—C11—H111	109.6	H191—C19—H192	108.3
C12—C11—H111	109.6	C14—N4—C8	117.3
C10—C11—H112	109.6	C14—N4—H01	108.0
C12—C11—H112	109.6	C8—N4—H01	108.0
H111—C11—H112	108.2	C14—N4—H02	108.0
C13—C12—C11	111.1	C8—N4—H02	108.0
C13—C12—H121	109.4	H01—N4—H02	107.2
C11—C12—H121	109.4	O1—C7—O2	126.0
C13—C12—H122	109.4	O1—C7—C3	117.8
C11—C12—H122	109.4	O2—C7—C3	116.2
H121—C12—H122	108.0	C6—C1—C2	120.7
C8—C13—C12	111.2	C6—C1—N1	114.9
C8—C13—H131	109.4	C2—C1—N1	124.4
C12—C13—H131	109.4	C3—C2—C1	119.4
C8—C13—H132	109.4	C3—C2—H2	120.3
C12—C13—H132	109.4	C1—C2—H2	120.3
H131—C13—H132	108.0	C4—C3—C2	119.9
N4—C14—C19	112.6	C4—C3—C7	119.3
N4—C14—C15	108.1	C2—C3—C7	120.8
C19—C14—C15	111.0	C3—C4—C5	120.2
N4—C14—H14	108.3	C3—C4—H4	119.9
C19—C14—H14	108.3	C5—C4—H4	119.9
C15—C14—H14	108.3	C6—C5—C4	120.2
C14—C15—C16	111.0	C6—C5—H5	119.9
C14—C15—H151	109.4	C4—C5—H5	119.9
C16—C15—H151	109.4	C5—C6—C1	119.7
C14—C15—H152	109.4	C5—C6—H6	120.2
C16—C15—H152	109.4	C1—C6—H6	120.2
H151—C15—H152	108.0	N2—N1—C1	117.2
C17—C16—C15	111.8	N2—N1—N1ⁱ	62.2
C17—C16—H161	109.2	C1—N1—N1ⁱ	66.6
C15—C16—H161	109.2	N3—N2—N1	171.7
C17—C16—H162	109.2

N4—C8—C9—C10	175.4	C6—C1—C2—C3	−0.7
C13—C8—C9—C10	55.2	N1—C1—C2—C3	179.5
C8—C9—C10—C11	−56.8	C1—C2—C3—C4	−0.1
C9—C10—C11—C12	57.5	C1—C2—C3—C7	179.1
C10—C11—C12—C13	−56.9	O1—C7—C3—C4	172.5
N4—C8—C13—C12	−177.3	O2—C7—C3—C4	−6.6
C9—C8—C13—C12	−54.9	O1—C7—C3—C2	−6.7
C11—C12—C13—C8	55.7	O2—C7—C3—C2	174.2
N4—C14—C15—C16	179.0	C2—C3—C4—C5	1.0
C19—C14—C15—C16	−57.1	C7—C3—C4—C5	−178.2
C14—C15—C16—C17	53.7	C3—C4—C5—C6	−1.1
C15—C16—C17—C18	−53.1	C4—C5—C6—C1	0.3
C16—C17—C18—C19	56.0	C2—C1—C6—C5	0.6
N4—C14—C19—C18	−179.6	N1—C1—C6—C5	−179.6
C15—C14—C19—C18	59.0	C6—C1—N1—N2	−174.4
C17—C18—C19—C14	−58.7	C2—C1—N1—N2	5.4
C19—C14—N4—C8	51.2	C6—C1—N1—N1ⁱ	148.2
C15—C14—N4—C8	174.2	C2—C1—N1—N1ⁱ	−32.0
C13—C8—N4—C14	178.8	C1—N1—N2—N3	175.5
C9—C8—N4—C14	56.3	N1ⁱ—N1—N2—N3	−145.4

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H01···O2ⁱⁱ	0.92	1.83	2.7266 (11)	164
N4—H02···O1ⁱⁱⁱ	0.92	1.89	2.7829 (10)	162

Symmetry codes: (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1.

N-benzyl-2-phenylethylammonium 4-azidebenzoate (4a-bp-f) top

Crystal data top

C₂₂H₂₂N₄O₂	Z = 2
M_r = 374.44	F(000) = 396
Triclinic, P1	D_x = 1.238 Mg m⁻³
a = 8.1100 (4) Å	Melting point: not measured K
b = 10.3363 (6) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.6177 (7) Å	Cell parameters from 3455 reflections
α = 72.377 (2)°	µ = 0.08 mm⁻¹
β = 73.542 (2)°	T = 92 K
γ = 70.583 (1)°	Plate, orange
V = 1004.67 (9) Å³	0.31 × 0.12 × 0.08 mm

Data collection top

Bruker SMART CCD area detector system diffractometer	5842 independent reflections
Radiation source: rotating anode	2789 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ω scans	θ_max = 30.0°, θ_min = 1.6°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −11→11
T_min = 0.975, T_max = 0.994	k = −14→14
16229 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: rigid model
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.257	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.1379P)²] where P = (F_o² + 2F_c²)/3
5842 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.39 e Å⁻³
9 restraints	Δρ_min = −0.29 e Å⁻³

Special details top

Experimental. 'photo-irradiated product 4,4'-dicarboxy-trans-azobenzene is observed'

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N4	0.75421 (9)	0.07769 (7)	0.06759 (6)	0.0446 (5)
H02	0.7892	0.0554	0.0030	0.054*
H01	0.8508	0.0911	0.0819	0.054*
C9	0.66968 (12)	0.33151 (8)	−0.01742 (8)	0.0476 (6)
C10	0.64971 (17)	0.35972 (10)	−0.12136 (8)	0.0545 (7)
H10	0.5969	0.3035	−0.1400	0.065*
C11	0.7063 (2)	0.46901 (11)	−0.19729 (9)	0.0777 (10)
H11	0.6918	0.4875	−0.2675	0.093*
C12	0.78317 (17)	0.55038 (10)	−0.17101 (11)	0.0898 (13)
H12	0.8205	0.6259	−0.2229	0.108*
C13	0.80663 (19)	0.52264 (9)	−0.06854 (13)	0.0897 (13)
H13	0.8619	0.5782	−0.0510	0.108*
C14	0.74868 (18)	0.41267 (8)	0.00912 (10)	0.0688 (9)
H14	0.7636	0.3942	0.0792	0.083*
C8	0.60626 (10)	0.21285 (8)	0.06255 (8)	0.0512 (7)
H81	0.5040	0.2006	0.0436	0.061*
H82	0.5650	0.2359	0.1325	0.061*
C17	0.81189 (13)	−0.29432 (8)	0.24343 (8)	0.0491 (6)
C18	0.84528 (18)	−0.30497 (10)	0.34111 (8)	0.0571 (7)
H18	0.8964	−0.2389	0.3486	0.069*
C19	0.8047 (2)	−0.41115 (11)	0.42781 (9)	0.0810 (11)
H19	0.8280	−0.4165	0.4937	0.097*
C20	0.73165 (19)	−0.50784 (10)	0.41883 (11)	0.1056 (16)
H20	0.7053	−0.5807	0.4779	0.127*
C21	0.69644 (19)	−0.49834 (10)	0.32262 (13)	0.1111 (17)
H21	0.6439	−0.5643	0.3163	0.133*
C22	0.73734 (18)	−0.39272 (8)	0.23467 (11)	0.0762 (10)
H22	0.7142	−0.3882	0.1689	0.091*
C15	0.69983 (9)	−0.04314 (8)	0.14962 (7)	0.0501 (6)
H151	0.5961	−0.0585	0.1347	0.060*
H152	0.6637	−0.0206	0.2196	0.060*
C16	0.85482 (11)	−0.17748 (7)	0.15058 (7)	0.0512 (6)
H161	0.8786	−0.2080	0.0845	0.061*
H162	0.9639	−0.1576	0.1543	0.061*
C1	0.75023 (14)	−0.00246 (10)	0.52593 (7)	0.0364 (6)	0.861 (5)
C2	0.66111 (13)	0.10162 (10)	0.58257 (7)	0.0365 (6)	0.861 (5)
H2	0.5719	0.1816	0.5565	0.044*	0.861 (5)
C3	0.70500 (15)	0.08645 (12)	0.67817 (8)	0.0340 (6)	0.861 (5)
H3	0.6444	0.1567	0.7174	0.041*	0.861 (5)
C4	0.83668 (14)	−0.03042 (13)	0.71721 (8)	0.0322 (6)	0.861 (5)
C5	0.92591 (17)	−0.13265 (13)	0.65840 (10)	0.0360 (6)	0.861 (5)
H5	1.0177	−0.2112	0.6833	0.043*	0.861 (5)
C6	0.88150 (18)	−0.12042 (12)	0.56367 (10)	0.0392 (6)	0.861 (5)
H6	0.9400	−0.1916	0.5252	0.047*	0.861 (5)
C7	0.88235 (19)	−0.04505 (17)	0.82118 (8)	0.0459 (8)	0.861 (5)
O1	0.7680 (2)	0.0291 (2)	0.88169 (9)	0.0561 (8)	0.861 (5)
O2	1.0305 (2)	−0.1281 (2)	0.83952 (11)	0.0689 (9)	0.861 (5)
N1	0.71382 (18)	0.00314 (12)	0.42732 (8)	0.0490 (7)	0.861 (5)
N2	0.61411 (19)	0.11663 (13)	0.38741 (8)	0.0510 (7)	0.912 (5)
N3	0.5251 (2)	0.21343 (15)	0.34306 (10)	0.0612 (8)	0.912 (5)
N1P	0.584 (3)	−0.038 (2)	0.4970 (17)	0.093 (7)*	0.149 (4)
C1P	0.664 (3)	−0.020 (2)	0.5724 (16)	0.069 (3)*	0.149 (4)
C2P	0.5979 (17)	0.0866 (14)	0.6273 (10)	0.069 (3)*	0.149 (4)
H2P	0.4983	0.1631	0.6100	0.083*	0.149 (4)
C3P	0.6762 (17)	0.0823 (14)	0.7072 (10)	0.069 (3)*	0.149 (4)
H3P	0.6285	0.1545	0.7452	0.083*	0.149 (4)
C4P	0.8243 (17)	−0.0275 (14)	0.7314 (10)	0.069 (3)*	0.149 (4)
C5P	0.8941 (17)	−0.1331 (14)	0.6758 (10)	0.069 (3)*	0.149 (4)
H5P	0.9954	−0.2082	0.6923	0.083*	0.149 (4)
C6P	0.8158 (17)	−0.1288 (14)	0.5959 (10)	0.069 (3)*	0.149 (4)
H6P	0.8655	−0.2000	0.5570	0.083*	0.149 (4)
C7P	0.899 (3)	−0.049 (3)	0.8276 (18)	0.069 (3)*	0.149 (4)
O1P	0.817 (3)	0.040 (2)	0.8849 (15)	0.069 (3)*	0.149 (4)
O2P	1.047 (2)	−0.142 (2)	0.8341 (13)	0.069 (3)*	0.149 (4)
N2P	0.636 (6)	0.217 (4)	0.318 (3)	0.096*	0.088 (5)
N3P	0.569 (5)	0.256 (4)	0.409 (3)	0.096*	0.088 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N4	0.0427 (11)	0.0379 (10)	0.0376 (10)	0.0104 (8)	−0.0154 (8)	−0.0034 (8)
C9	0.0371 (12)	0.0355 (12)	0.0514 (14)	0.0134 (10)	−0.0158 (10)	−0.0026 (10)
C10	0.0454 (14)	0.0448 (14)	0.0497 (14)	0.0107 (11)	−0.0159 (11)	0.0030 (11)
C11	0.0565 (18)	0.0593 (18)	0.0638 (18)	0.0174 (15)	−0.0041 (14)	0.0175 (14)
C12	0.0455 (17)	0.0444 (16)	0.130 (3)	0.0084 (13)	−0.0074 (19)	0.0177 (18)
C13	0.0418 (16)	0.0435 (17)	0.177 (4)	0.0116 (13)	−0.039 (2)	−0.025 (2)
C14	0.0516 (16)	0.0442 (15)	0.098 (2)	0.0189 (13)	−0.0366 (16)	−0.0134 (15)
C8	0.0482 (14)	0.0435 (13)	0.0403 (12)	0.0133 (11)	−0.0137 (11)	−0.0035 (10)
C17	0.0383 (12)	0.0313 (11)	0.0631 (16)	0.0084 (10)	−0.0124 (11)	−0.0079 (11)
C18	0.0619 (17)	0.0363 (13)	0.0554 (15)	0.0034 (12)	−0.0126 (13)	−0.0032 (11)
C19	0.073 (2)	0.0522 (17)	0.0685 (19)	0.0131 (15)	−0.0046 (16)	0.0139 (15)
C20	0.057 (2)	0.0459 (18)	0.153 (4)	0.0039 (16)	−0.002 (2)	0.026 (2)
C21	0.052 (2)	0.0429 (18)	0.221 (5)	−0.0114 (15)	−0.027 (3)	−0.007 (3)
C22	0.0476 (16)	0.0539 (17)	0.129 (3)	−0.0004 (14)	−0.0353 (18)	−0.0232 (19)
C15	0.0504 (14)	0.0385 (12)	0.0427 (13)	0.0072 (11)	−0.0111 (11)	−0.0027 (10)
C16	0.0520 (14)	0.0378 (13)	0.0474 (13)	0.0061 (11)	−0.0111 (11)	−0.0061 (10)
C1	0.0405 (15)	0.0331 (12)	0.0340 (13)	−0.0122 (11)	−0.0135 (11)	0.0027 (10)
C2	0.0334 (13)	0.0271 (12)	0.0414 (14)	−0.0033 (10)	−0.0153 (11)	0.0048 (10)
C3	0.0320 (12)	0.0265 (11)	0.0367 (13)	−0.0008 (9)	−0.0104 (10)	−0.0024 (10)
C4	0.0317 (12)	0.0274 (11)	0.0325 (12)	−0.0043 (9)	−0.0132 (10)	0.0020 (9)
C5	0.0301 (12)	0.0302 (12)	0.0396 (14)	0.0000 (10)	−0.0132 (10)	0.0002 (10)
C6	0.0418 (15)	0.0298 (12)	0.0385 (14)	−0.0028 (11)	−0.0092 (11)	−0.0040 (10)
C7	0.0582 (19)	0.0325 (13)	0.0396 (15)	0.0017 (13)	−0.0266 (13)	0.0020 (11)
O1	0.0684 (19)	0.0540 (14)	0.0393 (11)	0.0010 (13)	−0.0222 (11)	−0.0104 (10)
O2	0.0828 (18)	0.0487 (14)	0.0714 (16)	0.0262 (12)	−0.0602 (14)	−0.0158 (11)
N1	0.0603 (16)	0.0397 (13)	0.0458 (14)	−0.0055 (11)	−0.0279 (12)	−0.0013 (10)
N2	0.0608 (15)	0.0466 (14)	0.0474 (14)	−0.0173 (12)	−0.0231 (11)	0.0009 (11)
N3	0.077 (2)	0.0483 (14)	0.0594 (16)	−0.0210 (14)	−0.0386 (15)	0.0137 (12)

Geometric parameters (Å, º) top

N4—C15	1.4981	C16—H162	0.9900
N4—C8	1.5068	C1—C2	1.3943
N4—H02	0.9200	C1—C6	1.3970
N4—H01	0.9200	C1—N1	1.4353
C9—C14	1.3846	C2—C3	1.3957
C9—C10	1.4012	C2—H2	0.9500
C9—C8	1.4994	C3—C4	1.3991
C10—C11	1.3873	C3—H3	0.9500
C10—H10	0.9500	C4—C5	1.3990
C11—C12	1.3716	C4—C7	1.5149
C11—H11	0.9500	C5—C6	1.3943
C12—C13	1.3920	C5—H5	0.9500
C12—H12	0.9500	C6—H6	0.9500
C13—C14	1.4060	C7—O2	1.2641
C13—H13	0.9500	C7—O1	1.2662
C14—H14	0.9500	N1—N2	1.2481
C8—H81	0.9900	N2—N3	1.1349
C8—H82	0.9900	N1P—N1Pⁱ	1.33 (4)
C17—C22	1.3920	N1P—C1P	1.44 (3)
C17—C18	1.3965	C1P—C2P	1.39 (3)
C17—C16	1.5113	C1P—C6P	1.41 (3)
C18—C19	1.3935	C2P—C3P	1.3900
C18—H18	0.9500	C2P—H2P	0.9500
C19—C20	1.3690	C3P—C4P	1.3900
C19—H19	0.9500	C3P—H3P	0.9500
C20—C21	1.3868	C4P—C5P	1.3900
C20—H20	0.9500	C4P—C7P	1.52 (3)
C21—C22	1.4002	C5P—C6P	1.3900
C21—H21	0.9500	C5P—H5P	0.9500
C22—H22	0.9500	C6P—H6P	0.9500
C15—C16	1.5316	C7P—O2P	1.267 (16)
C15—H151	0.9900	C7P—O1P	1.280 (16)
C15—H152	0.9900	N2P—N3P	1.32 (5)
C16—H161	0.9900

C15—N4—C8	112.7	C17—C16—C15	110.9
C15—N4—H02	109.0	C17—C16—H161	109.5
C8—N4—H02	109.0	C15—C16—H161	109.5
C15—N4—H01	109.0	C17—C16—H162	109.5
C8—N4—H01	109.0	C15—C16—H162	109.5
H02—N4—H01	107.8	H161—C16—H162	108.1
C14—C9—C10	119.5	C2—C1—C6	120.9
C14—C9—C8	121.4	C2—C1—N1	123.1
C10—C9—C8	119.1	C6—C1—N1	116.0
C11—C10—C9	120.6	C1—C2—C3	118.9
C11—C10—H10	119.7	C1—C2—H2	120.5
C9—C10—H10	119.7	C3—C2—H2	120.5
C12—C11—C10	120.0	C2—C3—C4	121.1
C12—C11—H11	120.0	C2—C3—H3	119.4
C10—C11—H11	120.0	C4—C3—H3	119.4
C11—C12—C13	120.2	C5—C4—C3	118.9
C11—C12—H12	119.9	C5—C4—C7	120.7
C13—C12—H12	119.9	C3—C4—C7	120.3
C12—C13—C14	120.2	C6—C5—C4	120.7
C12—C13—H13	119.9	C6—C5—H5	119.7
C14—C13—H13	119.9	C4—C5—H5	119.7
C9—C14—C13	119.5	C5—C6—C1	119.4
C9—C14—H14	120.3	C5—C6—H6	120.3
C13—C14—H14	120.3	C1—C6—H6	120.3
C9—C8—N4	110.6	O2—C7—O1	125.8
C9—C8—H81	109.5	O2—C7—C4	117.7
N4—C8—H81	109.5	O1—C7—C4	116.4
C9—C8—H82	109.5	N2—N1—C1	115.5
N4—C8—H82	109.5	N2—N1—N1ⁱ	75.18 (8)
H81—C8—H82	108.1	C1—N1—N1ⁱ	84.45 (5)
C22—C17—C18	118.3	N3—N2—N1	172.9
C22—C17—C16	121.5	N1Pⁱ—N1P—C1P	111 (2)
C18—C17—C16	120.2	C2P—C1P—C6P	118.8 (18)
C19—C18—C17	120.9	C2P—C1P—N1P	126.8 (19)
C19—C18—H18	119.5	C6P—C1P—N1P	114.2 (18)
C17—C18—H18	119.5	C3P—C2P—C1P	120.7 (10)
C20—C19—C18	120.5	C3P—C2P—H2P	119.6
C20—C19—H19	119.7	C1P—C2P—H2P	119.6
C18—C19—H19	119.7	C4P—C3P—C2P	120.0
C19—C20—C21	119.3	C4P—C3P—H3P	120.0
C19—C20—H20	120.3	C2P—C3P—H3P	120.0
C21—C20—H20	120.3	C5P—C4P—C3P	120.0
C20—C21—C22	120.8	C5P—C4P—C7P	117.2 (9)
C20—C21—H21	119.6	C3P—C4P—C7P	122.2 (9)
C22—C21—H21	119.6	C4P—C5P—C6P	120.0
C17—C22—C21	120.1	C4P—C5P—H5P	120.0
C17—C22—H22	120.0	C6P—C5P—H5P	120.0
C21—C22—H22	120.0	C5P—C6P—C1P	120.4 (11)
N4—C15—C16	110.3	C5P—C6P—H6P	119.8
N4—C15—H151	109.6	C1P—C6P—H6P	119.8
C16—C15—H151	109.6	O2P—C7P—O1P	128 (2)
N4—C15—H152	109.6	O2P—C7P—C4P	115.9 (15)
C16—C15—H152	109.6	O1P—C7P—C4P	115.7 (18)
H151—C15—H152	108.1

C14—C9—C10—C11	−0.8	C4—C5—C6—C1	2.0
C8—C9—C10—C11	179.8	C2—C1—C6—C5	−1.2
C9—C10—C11—C12	0.2	N1—C1—C6—C5	179.3
C10—C11—C12—C13	0.8	C5—C4—C7—O2	18.6
C11—C12—C13—C14	−1.2	C3—C4—C7—O2	−161.0
C10—C9—C14—C13	0.4	C5—C4—C7—O1	−162.1
C8—C9—C14—C13	179.8	C3—C4—C7—O1	18.3
C12—C13—C14—C9	0.6	C2—C1—N1—N2	9.4
C14—C9—C8—N4	−88.6	C6—C1—N1—N2	−171.0
C10—C9—C8—N4	90.9	C2—C1—N1—N1ⁱ	−61.23 (10)
C15—N4—C8—C9	177.6	C6—C1—N1—N1ⁱ	118.35 (10)
C22—C17—C18—C19	−0.1	C1—N1—N2—N3	−178.2
C16—C17—C18—C19	179.3	N1ⁱ—N1—N2—N3	−101.95 (7)
C17—C18—C19—C20	0.2	N1Pⁱ—N1P—C1P—C2P	−15 (3)
C18—C19—C20—C21	−0.7	N1Pⁱ—N1P—C1P—C6P	160 (2)
C19—C20—C21—C22	1.0	C6P—C1P—C2P—C3P	−2.8 (14)
C18—C17—C22—C21	0.5	N1P—C1P—C2P—C3P	172.1 (13)
C16—C17—C22—C21	−179.0	C1P—C2P—C3P—C4P	1.5 (7)
C20—C21—C22—C17	−0.9	C2P—C3P—C4P—C5P	0.0
C8—N4—C15—C16	179.6	C2P—C3P—C4P—C7P	−171.2 (11)
C22—C17—C16—C15	93.7	C3P—C4P—C5P—C6P	0.0
C18—C17—C16—C15	−85.7	C7P—C4P—C5P—C6P	171.6 (10)
N4—C15—C16—C17	171.3	C4P—C5P—C6P—C1P	−1.4 (7)
C6—C1—C2—C3	0.0	C2P—C1P—C6P—C5P	2.8 (14)
N1—C1—C2—C3	179.6	N1P—C1P—C6P—C5P	−172.8 (11)
C1—C2—C3—C4	0.3	C5P—C4P—C7P—O2P	17 (2)
C2—C3—C4—C5	0.5	C3P—C4P—C7P—O2P	−172.0 (13)
C2—C3—C4—C7	−180.0	C5P—C4P—C7P—O1P	−171.2 (15)
C3—C4—C5—C6	−1.6	C3P—C4P—C7P—O1P	0 (2)
C7—C4—C5—C6	178.8

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H02···O1ⁱⁱ	0.92	1.82	2.6920 (14)	158
N4—H01···O2ⁱⁱⁱ	0.92	1.81	2.678 (2)	155

Symmetry codes: (ii) x, y, z−1; (iii) −x+2, −y, −z+1.

(Dibenzylammonium 4-azidebenzoate) 4-azidebenzoic acid clathrate (4a-db-I-i) top

Crystal data top

C₂₈H₂₅N₇O₄	F(000) = 1096
M_r = 523.55	D_x = 1.347 Mg m⁻³
Monoclinic, P2₁/n	Melting point: not measured K
a = 10.4763 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2909 (5) Å	Cell parameters from 8192 reflections
c = 26.8857 (13) Å	µ = 0.09 mm⁻¹
β = 99.468 (2)°	T = 88 K
V = 2581.3 (2) Å³	Block, pale-yellow
Z = 4	0.38 × 0.36 × 0.10 mm

Data collection top

Bruker SMART CCD area detector system diffractometer	7514 independent reflections
Radiation source: rotating-anode	6237 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 30.0°, θ_min = 1.5°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −14→14
T_min = 0.965, T_max = 0.991	k = −13→13
40617 measured reflections	l = −37→37

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.105	Only H-atom coordinates refined
S = 1.10	w = 1/[σ²(F_o²) + (0.0602P)² + 0.2618P] where P = (F_o² + 2F_c²)/3
7514 reflections	(Δ/σ)_max = 0.001
428 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C7A	0.91063 (8)	0.46223 (9)	0.19194 (3)	0.01394 (16)
C1A	1.10690 (9)	0.58437 (10)	0.06960 (3)	0.01712 (17)
C2A	1.06942 (9)	0.44159 (10)	0.07395 (3)	0.01835 (18)
H2A	1.0847 (12)	0.3665 (15)	0.0488 (5)	0.022*
C3A	1.00551 (9)	0.40244 (10)	0.11346 (3)	0.01661 (17)
H3A	0.9783 (12)	0.3030 (14)	0.1158 (5)	0.020*
C4A	0.98124 (8)	0.50317 (10)	0.14931 (3)	0.01424 (16)
C5A	1.02282 (9)	0.64470 (10)	0.14501 (4)	0.01730 (17)
H5A	1.0096 (12)	0.7167 (14)	0.1699 (5)	0.021*
C6A	1.08359 (9)	0.68633 (10)	0.10507 (4)	0.01887 (18)
H6A	1.1082 (13)	0.7868 (15)	0.1012 (5)	0.023*
N1A	1.17086 (9)	0.63625 (10)	0.02999 (3)	0.02252 (17)
N2A	1.20732 (9)	0.54155 (10)	0.00269 (3)	0.02396 (18)
N3A	1.24501 (11)	0.46644 (12)	−0.02456 (4)	0.0358 (2)
O2A	0.85798 (6)	0.33725 (7)	0.19006 (2)	0.01610 (13)
O1A	0.90660 (7)	0.54922 (7)	0.22693 (2)	0.01814 (14)
C7B	0.60372 (9)	0.19720 (10)	0.11843 (4)	0.01812 (18)
C1B	0.32340 (9)	0.10927 (10)	−0.01213 (4)	0.01995 (19)
C2B	0.29438 (10)	0.08144 (12)	0.03577 (4)	0.0246 (2)
H2B	0.2112 (14)	0.0394 (16)	0.0396 (5)	0.030*
C3B	0.38688 (10)	0.11122 (12)	0.07777 (4)	0.0238 (2)
H3B	0.3691 (13)	0.0908 (15)	0.1112 (5)	0.029*
C4B	0.50712 (9)	0.16822 (10)	0.07230 (3)	0.01788 (18)
C5B	0.53386 (10)	0.19668 (10)	0.02400 (4)	0.01860 (18)
H5B	0.6190 (13)	0.2338 (14)	0.0201 (5)	0.022*
C6B	0.44223 (10)	0.16719 (10)	−0.01823 (4)	0.01978 (18)
H6B	0.4618 (13)	0.1807 (14)	−0.0525 (5)	0.024*
N1B	0.23633 (9)	0.07975 (10)	−0.05782 (3)	0.02518 (18)
N2B	0.13687 (9)	0.01086 (10)	−0.05374 (3)	0.02553 (19)
N3B	0.04313 (10)	−0.05135 (13)	−0.05600 (4)	0.0361 (2)
O1B	0.71772 (7)	0.24175 (8)	0.10853 (3)	0.02112 (15)
O2B	0.57967 (8)	0.18208 (8)	0.16103 (3)	0.02374 (16)
H03	0.7653 (17)	0.2723 (19)	0.1373 (7)	0.047 (5)*
C8	0.89352 (9)	0.93862 (10)	0.25916 (3)	0.01663 (17)
H81	0.9117 (12)	0.9182 (14)	0.2947 (5)	0.020*
H82	0.8463 (12)	1.0286 (15)	0.2534 (5)	0.020*
C9	1.01782 (9)	0.94611 (9)	0.23779 (3)	0.01529 (16)
C10	1.03023 (9)	1.03984 (10)	0.19847 (4)	0.01833 (18)
H10	0.9559 (13)	1.0958 (14)	0.1825 (5)	0.022*
C11	1.14928 (10)	1.05688 (11)	0.18230 (4)	0.02173 (19)
H11	1.1572 (13)	1.1247 (15)	0.1547 (5)	0.026*
C12	1.25692 (10)	0.98118 (11)	0.20575 (4)	0.0229 (2)
H12	1.3408 (14)	0.9970 (15)	0.1948 (5)	0.027*
C13	1.24458 (10)	0.88448 (11)	0.24428 (4)	0.02218 (19)
H13	1.3206 (13)	0.8313 (15)	0.2605 (5)	0.027*
C14	1.12543 (9)	0.86654 (11)	0.26017 (4)	0.01892 (18)
H14	1.1171 (13)	0.8029 (15)	0.2880 (5)	0.023*
C15	0.73730 (9)	0.85791 (10)	0.18389 (3)	0.01673 (17)
H151	0.8073 (12)	0.8605 (14)	0.1628 (5)	0.020*
H152	0.6986 (12)	0.9539 (14)	0.1842 (5)	0.020*
C16	0.63326 (8)	0.75101 (10)	0.16403 (3)	0.01482 (16)
C17	0.65232 (9)	0.64938 (10)	0.12780 (3)	0.01572 (17)
H17	0.7369 (12)	0.6470 (14)	0.1153 (5)	0.019*
C18	0.55284 (9)	0.55533 (10)	0.10825 (3)	0.01768 (17)
H18	0.5686 (12)	0.4851 (14)	0.0824 (5)	0.021*
C19	0.43450 (9)	0.56155 (11)	0.12530 (4)	0.01989 (18)
H19	0.3654 (13)	0.4947 (15)	0.1123 (5)	0.024*
C20	0.41478 (9)	0.66225 (11)	0.16165 (4)	0.02147 (19)
H20	0.3313 (13)	0.6628 (15)	0.1733 (5)	0.026*
C21	0.51389 (9)	0.75676 (11)	0.18081 (4)	0.01876 (18)
H21	0.5023 (12)	0.8293 (15)	0.2062 (5)	0.023*
N4	0.80110 (7)	0.82311 (8)	0.23663 (3)	0.01398 (14)
H02	0.8400 (12)	0.7338 (14)	0.2377 (5)	0.017*
H01	0.7379 (12)	0.8174 (13)	0.2588 (5)	0.017*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7A	0.0122 (4)	0.0158 (4)	0.0134 (4)	0.0033 (3)	0.0009 (3)	0.0002 (3)
C1A	0.0147 (4)	0.0219 (4)	0.0150 (4)	0.0006 (3)	0.0032 (3)	0.0008 (3)
C2A	0.0194 (4)	0.0204 (4)	0.0161 (4)	0.0012 (3)	0.0054 (3)	−0.0028 (3)
C3A	0.0182 (4)	0.0157 (4)	0.0163 (4)	0.0007 (3)	0.0040 (3)	−0.0016 (3)
C4A	0.0131 (4)	0.0165 (4)	0.0131 (4)	0.0015 (3)	0.0017 (3)	−0.0009 (3)
C5A	0.0170 (4)	0.0172 (4)	0.0179 (4)	−0.0003 (3)	0.0039 (3)	−0.0030 (3)
C6A	0.0187 (4)	0.0177 (4)	0.0207 (4)	−0.0021 (3)	0.0047 (3)	−0.0013 (3)
N1A	0.0251 (4)	0.0249 (4)	0.0194 (4)	−0.0011 (3)	0.0092 (3)	0.0004 (3)
N2A	0.0234 (4)	0.0295 (4)	0.0207 (4)	0.0016 (3)	0.0089 (3)	0.0040 (3)
N3A	0.0434 (6)	0.0393 (6)	0.0300 (5)	0.0088 (5)	0.0215 (4)	0.0027 (4)
O2A	0.0169 (3)	0.0162 (3)	0.0154 (3)	−0.0005 (2)	0.0030 (2)	−0.0009 (2)
O1A	0.0211 (3)	0.0182 (3)	0.0156 (3)	0.0019 (2)	0.0044 (2)	−0.0029 (2)
C7B	0.0212 (4)	0.0149 (4)	0.0176 (4)	0.0013 (3)	0.0013 (3)	−0.0002 (3)
C1B	0.0209 (4)	0.0182 (4)	0.0191 (4)	0.0021 (3)	−0.0017 (3)	−0.0009 (3)
C2B	0.0192 (4)	0.0319 (5)	0.0226 (5)	−0.0034 (4)	0.0035 (4)	−0.0032 (4)
C3B	0.0223 (5)	0.0316 (5)	0.0180 (4)	−0.0022 (4)	0.0052 (4)	−0.0021 (4)
C4B	0.0195 (4)	0.0171 (4)	0.0163 (4)	0.0013 (3)	0.0008 (3)	−0.0011 (3)
C5B	0.0214 (4)	0.0155 (4)	0.0183 (4)	−0.0010 (3)	0.0016 (3)	0.0019 (3)
C6B	0.0247 (5)	0.0166 (4)	0.0169 (4)	0.0000 (3)	0.0003 (3)	0.0027 (3)
N1B	0.0247 (4)	0.0270 (4)	0.0214 (4)	−0.0036 (3)	−0.0037 (3)	0.0004 (3)
N2B	0.0235 (4)	0.0285 (4)	0.0226 (4)	0.0012 (3)	−0.0021 (3)	−0.0045 (3)
N3B	0.0262 (5)	0.0469 (6)	0.0336 (5)	−0.0074 (4)	0.0001 (4)	−0.0089 (5)
O1B	0.0200 (3)	0.0252 (4)	0.0174 (3)	−0.0019 (3)	0.0009 (3)	−0.0041 (3)
O2B	0.0291 (4)	0.0257 (4)	0.0161 (3)	−0.0027 (3)	0.0026 (3)	0.0012 (3)
C8	0.0158 (4)	0.0176 (4)	0.0171 (4)	−0.0034 (3)	0.0045 (3)	−0.0060 (3)
C9	0.0153 (4)	0.0149 (4)	0.0161 (4)	−0.0013 (3)	0.0039 (3)	−0.0044 (3)
C10	0.0168 (4)	0.0161 (4)	0.0225 (4)	0.0023 (3)	0.0046 (3)	0.0006 (3)
C11	0.0212 (4)	0.0194 (4)	0.0263 (5)	0.0019 (3)	0.0091 (4)	0.0045 (4)
C12	0.0185 (4)	0.0232 (5)	0.0289 (5)	0.0025 (4)	0.0095 (4)	0.0017 (4)
C13	0.0177 (4)	0.0241 (5)	0.0247 (5)	0.0050 (4)	0.0034 (4)	0.0024 (4)
C14	0.0196 (4)	0.0201 (4)	0.0172 (4)	0.0014 (3)	0.0035 (3)	0.0007 (3)
C15	0.0183 (4)	0.0180 (4)	0.0133 (4)	−0.0010 (3)	0.0007 (3)	0.0016 (3)
C16	0.0151 (4)	0.0159 (4)	0.0127 (4)	0.0019 (3)	0.0000 (3)	0.0021 (3)
C17	0.0166 (4)	0.0175 (4)	0.0132 (4)	0.0021 (3)	0.0026 (3)	0.0021 (3)
C18	0.0215 (4)	0.0166 (4)	0.0139 (4)	0.0015 (3)	−0.0003 (3)	0.0010 (3)
C19	0.0174 (4)	0.0213 (4)	0.0191 (4)	−0.0019 (3)	−0.0026 (3)	0.0023 (3)
C20	0.0135 (4)	0.0287 (5)	0.0218 (4)	0.0025 (4)	0.0018 (3)	0.0018 (4)
C21	0.0160 (4)	0.0231 (4)	0.0168 (4)	0.0047 (3)	0.0017 (3)	−0.0012 (3)
N4	0.0146 (3)	0.0149 (3)	0.0123 (3)	−0.0004 (3)	0.0019 (3)	−0.0011 (3)

Geometric parameters (Å, º) top

C7A—O1A	1.2462 (11)	C8—N4	1.5044 (11)
C7A—O2A	1.2829 (11)	C8—C9	1.5090 (12)
C7A—C4A	1.5115 (12)	C8—H81	0.961 (13)
C1A—C2A	1.3938 (13)	C8—H82	0.971 (13)
C1A—C6A	1.3939 (13)	C9—C10	1.3921 (13)
C1A—N1A	1.4320 (12)	C9—C14	1.3987 (13)
C2A—C3A	1.3939 (13)	C10—C11	1.3957 (13)
C2A—H2A	1.003 (13)	C10—H10	0.975 (13)
C3A—C4A	1.3965 (12)	C11—C12	1.3892 (14)
C3A—H3A	0.972 (13)	C11—H11	0.987 (14)
C4A—C5A	1.3960 (13)	C12—C13	1.3931 (14)
C5A—C6A	1.3903 (13)	C12—H12	0.983 (14)
C5A—H5A	0.973 (13)	C13—C14	1.3943 (14)
C6A—H6A	0.979 (14)	C13—H13	0.977 (14)
N1A—N2A	1.2453 (12)	C14—H14	0.969 (14)
N2A—N3A	1.1291 (13)	C15—N4	1.5000 (11)
C7B—O2B	1.2209 (12)	C15—C16	1.5060 (13)
C7B—O1B	1.3315 (12)	C15—H151	0.999 (13)
C7B—C4B	1.4905 (13)	C15—H152	0.980 (13)
C1B—C6B	1.3905 (14)	C16—C17	1.3944 (12)
C1B—C2B	1.3951 (14)	C16—C21	1.3986 (13)
C1B—N1B	1.4310 (13)	C17—C18	1.3949 (13)
C2B—C3B	1.3897 (14)	C17—H17	0.998 (13)
C2B—H2B	0.976 (15)	C18—C19	1.3919 (14)
C3B—C4B	1.3964 (14)	C18—H18	0.987 (13)
C3B—H3B	0.967 (14)	C19—C20	1.3927 (14)
C4B—C5B	1.3982 (13)	C19—H19	0.974 (14)
C5B—C6B	1.3880 (13)	C20—C21	1.3924 (14)
C5B—H5B	0.978 (13)	C20—H20	0.976 (14)
C6B—H6B	0.986 (14)	C21—H21	0.981 (14)
N1B—N2B	1.2431 (13)	N4—H02	0.923 (13)
N2B—N3B	1.1325 (14)	N4—H01	0.963 (13)
O1B—H03	0.895 (18)

O1A—C7A—O2A	123.30 (8)	C9—C8—H82	110.4 (8)
O1A—C7A—C4A	119.39 (8)	H81—C8—H82	109.9 (11)
O2A—C7A—C4A	117.31 (8)	C10—C9—C14	119.21 (8)
C2A—C1A—C6A	120.40 (8)	C10—C9—C8	120.81 (8)
C2A—C1A—N1A	123.74 (8)	C14—C9—C8	119.79 (8)
C6A—C1A—N1A	115.86 (8)	C9—C10—C11	120.48 (9)
C1A—C2A—C3A	119.31 (8)	C9—C10—H10	120.0 (8)
C1A—C2A—H2A	121.8 (8)	C11—C10—H10	119.5 (8)
C3A—C2A—H2A	118.9 (8)	C12—C11—C7A	120.10 (9)
C2A—C3A—C4A	121.06 (9)	C12—C11—H11	120.1 (8)
C2A—C3A—H3A	118.8 (8)	C10—C11—H11	119.8 (8)
C4A—C3A—H3A	120.2 (8)	C11—C12—C13	119.75 (9)
C5A—C4A—C3A	118.64 (8)	C11—C12—H12	119.2 (8)
C5A—C4A—C7A	119.88 (8)	C13—C12—H12	121.1 (8)
C3A—C4A—C7A	121.48 (8)	C12—C13—C14	120.14 (9)
C6A—C5A—C4A	120.98 (8)	C12—C13—H13	119.4 (8)
C6A—C5A—H5A	118.4 (8)	C14—C13—H13	120.4 (8)
C4A—C5A—H5A	120.6 (8)	C13—C14—C9	120.26 (9)
C5A—C6A—C1A	119.56 (9)	C13—C14—H14	120.6 (8)
C5A—C6A—H6A	120.6 (8)	C9—C14—H14	119.1 (8)
C1A—C6A—H6A	119.8 (8)	N4—C15—C16	112.15 (7)
N2A—N1A—C1A	115.27 (9)	N4—C15—H151	106.7 (7)
N3A—N2A—N1A	173.20 (11)	C16—C15—H151	111.7 (7)
O2B—C7B—O1B	123.62 (9)	N4—C15—H152	108.0 (8)
O2B—C7B—C4B	122.90 (9)	C16—C15—H152	109.1 (8)
O1B—C7B—C4B	113.48 (8)	H151—C15—H152	109.1 (11)
C6B—C1B—C2B	121.06 (9)	C17—C16—C21	119.32 (8)
C6B—C1B—N1B	115.44 (9)	C17—C16—C15	121.06 (8)
C2B—C1B—N1B	123.50 (9)	C21—C16—C15	119.59 (8)
C3B—C2B—C1B	118.98 (9)	C16—C17—C18	120.23 (8)
C3B—C2B—H2B	120.6 (8)	C16—C17—H17	119.2 (7)
C1B—C2B—H2B	120.4 (8)	C18—C17—H17	120.6 (7)
C2B—C3B—C4B	120.70 (9)	C19—C18—C17	120.04 (9)
C2B—C3B—H3B	120.1 (8)	C19—C18—H18	121.4 (8)
C4B—C3B—H3B	119.2 (8)	C17—C18—H18	118.6 (8)
C3B—C4B—C5B	119.44 (9)	C18—C19—C20	120.14 (9)
C3B—C4B—C7B	118.80 (9)	C18—C19—H19	120.3 (8)
C5B—C4B—C7B	121.76 (9)	C20—C19—H19	119.6 (8)
C6B—C5B—C4B	120.34 (9)	C21—C20—C19	119.71 (9)
C6B—C5B—H5B	120.1 (8)	C21—C20—H20	122.0 (8)
C4B—C5B—H5B	119.5 (8)	C19—C20—H20	118.2 (8)
C5B—C6B—C1B	119.47 (9)	C20—C21—C16	120.56 (9)
C5B—C6B—H6B	121.2 (8)	C20—C21—H21	121.4 (8)
C1B—C6B—H6B	119.2 (8)	C16—C21—H21	118.1 (8)
N2B—N1B—C1B	116.62 (9)	C15—N4—C8	112.59 (7)
N3B—N2B—N1B	171.96 (11)	C15—N4—H02	110.4 (8)
C7B—O1B—H03	108.4 (11)	C8—N4—H02	112.2 (8)
N4—C8—C9	114.71 (7)	C15—N4—H01	110.6 (8)
N4—C8—H81	105.5 (8)	C8—N4—H01	104.7 (7)
C9—C8—H81	110.2 (8)	H02—N4—H01	106.1 (11)
N4—C8—H82	105.8 (8)

C6A—C1A—C2A—C3A	1.55 (14)	C4B—C5B—C6B—C1B	0.10 (14)
N1A—C1A—C2A—C3A	−178.83 (9)	C2B—C1B—C6B—C5B	0.54 (15)
C1A—C2A—C3A—C4A	−1.50 (14)	N1B—C1B—C6B—C5B	−178.75 (9)
C2A—C3A—C4A—C5A	−0.25 (13)	C6B—C1B—N1B—N2B	170.83 (9)
C2A—C3A—C4A—C7A	179.27 (8)	C2B—C1B—N1B—N2B	−8.44 (15)
O1A—C7A—C4A—C5A	−10.38 (12)	C1B—N1B—N2B—N3B	−176.8 (8)
O2A—C7A—C4A—C5A	169.99 (8)	N4—C8—C9—C10	94.46 (10)
O1A—C7A—C4A—C3A	170.10 (8)	N4—C8—C9—C14	−90.60 (10)
O2A—C7A—C4A—C3A	−9.53 (12)	C14—C9—C10—C11	−1.48 (14)
C3A—C4A—C5A—C6A	1.99 (14)	C8—C9—C10—C11	173.49 (9)
C7A—C4A—C5A—C6A	−177.54 (8)	C9—C10—C11—C12	−0.63 (15)
C4A—C5A—C6A—C1A	−1.95 (14)	C7A—C11—C12—C13	2.23 (16)
C2A—C1A—C6A—C5A	0.15 (14)	C11—C12—C13—C14	−1.70 (16)
N1A—C1A—C6A—C5A	−179.50 (9)	C12—C13—C14—C9	−0.42 (15)
C2A—C1A—N1A—N2A	−9.23 (14)	C10—C9—C14—C13	2.01 (14)
C6A—C1A—N1A—N2A	170.40 (9)	C8—C9—C14—C13	−173.02 (9)
C1A—N1A—N2A—N3A	−179 (100)	N4—C15—C16—C17	−106.64 (9)
C6B—C1B—C2B—C3B	−0.62 (16)	N4—C15—C16—C21	75.63 (10)
N1B—C1B—C2B—C3B	178.61 (10)	C21—C16—C17—C18	0.53 (13)
C1B—C2B—C3B—C4B	0.05 (17)	C15—C16—C17—C18	−177.21 (8)
C2B—C3B—C4B—C5B	0.58 (16)	C16—C17—C18—C19	−0.74 (13)
C2B—C3B—C4B—C7B	−179.46 (10)	C17—C18—C19—C20	0.44 (14)
O2B—C7B—C4B—C3B	−4.87 (15)	C18—C19—C20—C21	0.07 (14)
O1B—C7B—C4B—C3B	175.53 (9)	C19—C20—C21—C16	−0.28 (15)
O2B—C7B—C4B—C5B	175.09 (9)	C17—C16—C21—C20	−0.02 (14)
O1B—C7B—C4B—C5B	−4.50 (13)	C15—C16—C21—C20	177.75 (9)
C3B—C4B—C5B—C6B	−0.65 (15)	C16—C15—N4—C8	−172.97 (7)
C7B—C4B—C5B—C6B	179.38 (9)	C9—C8—N4—C15	−72.50 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H03···O2A	0.895 (18)	1.692 (19)	2.5869 (10)	177.0 (17)
N4—H02···O1A	0.923 (13)	1.891 (13)	2.8036 (10)	169.3 (12)
N4—H01···O2Aⁱ	0.963 (13)	1.840 (13)	2.7856 (10)	166.5 (11)

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

Dibenzylammonium 4-azidebenzoate (4a-db-II-i) top

Crystal data top

C₂₁H₂₀N₄O₂	D_x = 1.258 Mg m⁻³
M_r = 360.41	Melting point: not measured K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71075 Å
a = 8.9331 (3) Å	Cell parameters from 35949 reflections
b = 16.5714 (7) Å	µ = 0.08 mm⁻¹
c = 25.7127 (9) Å	T = 78 K
V = 3806.4 (2) Å³	Needle, pale-yellow
Z = 8	0.42 × 0.17 × 0.16 mm
F(000) = 1520

Data collection top

Rigaku RAXIS-RAPID IP area detector system diffractometer	4248 independent reflections
Radiation source: rotating anode	3698 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Oscillation Photograph scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: empirical (using intensity measurements) ABSCOR (Higashi, 1995)	h = −11→10
T_min = 0.966, T_max = 0.987	k = −21→21
30191 measured reflections	l = −33→33

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)] = 0.054	Hydrogen site location: difference Fourier map
wR(F²) = 0.121	Only H-atom coordinates refined
S = 1.11	w = 1/[σ²(F_o²) + (0.0542P)² + 1.6574P] where P = (F_o² + 2F_c²)/3
4248 reflections	(Δ/σ)_max = 0.001
306 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.12430 (16)	0.03020 (10)	0.72512 (6)	0.0383 (4)
N2	0.01742 (16)	−0.00766 (9)	0.70645 (5)	0.0332 (3)
N3	−0.06905 (19)	−0.04387 (11)	0.68456 (6)	0.0458 (4)
O1	−0.07559 (11)	0.19827 (6)	0.93805 (4)	0.0235 (2)
O2	0.15512 (11)	0.24885 (7)	0.93047 (4)	0.0242 (2)
C7	0.04879 (14)	0.20548 (8)	0.91504 (5)	0.0188 (3)
C1	0.10044 (17)	0.07095 (10)	0.77354 (6)	0.0261 (3)
C2	0.21055 (17)	0.12507 (11)	0.78865 (6)	0.0298 (3)
H2	0.296 (2)	0.1330 (12)	0.7662 (7)	0.036*
C3	0.19369 (16)	0.16816 (10)	0.83439 (6)	0.0258 (3)
H3	0.270 (2)	0.2065 (12)	0.8443 (7)	0.031*
C4	0.06708 (15)	0.15822 (9)	0.86524 (5)	0.0197 (3)
C5	−0.04116 (15)	0.10289 (9)	0.84970 (5)	0.0226 (3)
H5	−0.1291 (19)	0.0960 (11)	0.8702 (7)	0.027*
C6	−0.02439 (16)	0.05822 (10)	0.80451 (6)	0.0246 (3)
H6	−0.101 (2)	0.0202 (12)	0.7948 (7)	0.030*
N4	0.44817 (12)	0.24645 (7)	0.96608 (4)	0.0174 (2)
H02	0.354 (2)	0.2461 (12)	0.9510 (7)	0.033 (5)*
H01	0.436 (2)	0.2608 (13)	1.0023 (8)	0.039 (5)*
C8	0.51709 (16)	0.16455 (9)	0.96173 (6)	0.0223 (3)
H81	0.610 (2)	0.1673 (11)	0.9804 (7)	0.027*
H82	0.5374 (18)	0.1534 (11)	0.9237 (7)	0.027*
C9	0.41222 (15)	0.10255 (8)	0.98438 (5)	0.0204 (3)
C10	0.40941 (16)	0.08806 (9)	1.03768 (6)	0.0235 (3)
H10	0.479 (2)	0.1172 (11)	1.0608 (7)	0.028*
C11	0.30891 (17)	0.03254 (10)	1.05826 (6)	0.0266 (3)
H11	0.3064 (19)	0.0236 (11)	1.0964 (7)	0.032*
C12	0.21058 (16)	−0.00860 (10)	1.02588 (7)	0.0281 (3)
H12	0.142 (2)	−0.0484 (12)	1.0398 (7)	0.034*
C13	0.21268 (17)	0.00630 (10)	0.97291 (6)	0.0284 (3)
H13	0.146 (2)	−0.0219 (12)	0.9498 (7)	0.034*
C14	0.31361 (16)	0.06112 (9)	0.95222 (6)	0.0248 (3)
H14	0.3155 (19)	0.0703 (11)	0.9147 (7)	0.030*
C15	0.54254 (16)	0.31284 (9)	0.94391 (5)	0.0207 (3)
H151	0.644 (2)	0.3049 (11)	0.9585 (6)	0.025*
H152	0.5000 (19)	0.3633 (11)	0.9574 (6)	0.025*
C16	0.54500 (15)	0.31313 (9)	0.88554 (5)	0.0210 (3)
C17	0.42758 (16)	0.34675 (9)	0.85731 (6)	0.0241 (3)
H17	0.345 (2)	0.3710 (11)	0.8752 (7)	0.029*
C18	0.42891 (19)	0.34448 (11)	0.80328 (6)	0.0313 (4)
H18	0.344 (2)	0.3694 (13)	0.7845 (7)	0.038*
C19	0.5472 (2)	0.30913 (13)	0.77727 (6)	0.0408 (4)
H19	0.548 (2)	0.3082 (13)	0.7397 (9)	0.049*
C20	0.6653 (2)	0.27688 (13)	0.80503 (7)	0.0430 (5)
H20	0.752 (3)	0.2542 (14)	0.7870 (8)	0.052*
C21	0.66453 (18)	0.27884 (11)	0.85895 (6)	0.0326 (4)
H21	0.750 (2)	0.2571 (12)	0.8785 (7)	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0317 (7)	0.0480 (9)	0.0354 (8)	−0.0120 (6)	0.0099 (6)	−0.0181 (7)
N2	0.0354 (7)	0.0375 (9)	0.0267 (7)	−0.0042 (6)	0.0048 (5)	−0.0079 (6)
N3	0.0476 (9)	0.0546 (11)	0.0351 (8)	−0.0123 (8)	−0.0022 (7)	−0.0150 (7)
O1	0.0204 (5)	0.0280 (6)	0.0222 (5)	−0.0029 (4)	0.0007 (4)	−0.0020 (4)
O2	0.0186 (5)	0.0245 (6)	0.0296 (5)	−0.0009 (4)	−0.0031 (4)	−0.0039 (4)
C7	0.0183 (6)	0.0180 (7)	0.0202 (6)	0.0016 (5)	−0.0038 (5)	0.0033 (5)
C1	0.0272 (7)	0.0278 (8)	0.0232 (7)	−0.0011 (6)	0.0020 (6)	−0.0041 (6)
C2	0.0240 (7)	0.0333 (9)	0.0322 (8)	−0.0063 (6)	0.0091 (6)	−0.0042 (6)
C3	0.0219 (7)	0.0257 (8)	0.0298 (7)	−0.0058 (6)	0.0028 (6)	−0.0028 (6)
C4	0.0186 (6)	0.0197 (7)	0.0207 (6)	0.0012 (5)	−0.0017 (5)	0.0027 (5)
C5	0.0187 (7)	0.0272 (8)	0.0217 (7)	−0.0022 (5)	0.0003 (5)	0.0021 (5)
C6	0.0208 (7)	0.0276 (8)	0.0253 (7)	−0.0042 (6)	−0.0023 (5)	−0.0013 (6)
N4	0.0156 (5)	0.0159 (6)	0.0206 (5)	−0.0004 (4)	0.0002 (4)	0.0004 (4)
C8	0.0198 (7)	0.0156 (7)	0.0314 (7)	0.0012 (5)	0.0032 (5)	0.0004 (5)
C9	0.0169 (6)	0.0145 (7)	0.0299 (7)	0.0031 (5)	0.0009 (5)	0.0007 (5)
C10	0.0209 (7)	0.0195 (7)	0.0301 (7)	0.0019 (5)	−0.0014 (5)	0.0008 (5)
C11	0.0260 (7)	0.0232 (8)	0.0306 (8)	0.0041 (6)	0.0027 (6)	0.0052 (6)
C12	0.0220 (7)	0.0178 (8)	0.0444 (9)	0.0009 (6)	0.0049 (6)	0.0062 (6)
C13	0.0238 (7)	0.0214 (8)	0.0401 (9)	−0.0038 (6)	−0.0052 (6)	−0.0005 (6)
C14	0.0244 (7)	0.0207 (8)	0.0292 (7)	0.0001 (5)	−0.0014 (6)	−0.0001 (6)
C15	0.0220 (7)	0.0171 (7)	0.0230 (7)	−0.0037 (5)	−0.0008 (5)	0.0008 (5)
C16	0.0209 (7)	0.0182 (7)	0.0238 (7)	−0.0044 (5)	0.0005 (5)	0.0028 (5)
C17	0.0224 (7)	0.0218 (8)	0.0281 (7)	−0.0012 (5)	−0.0013 (5)	0.0026 (6)
C18	0.0343 (8)	0.0317 (9)	0.0278 (8)	−0.0024 (7)	−0.0072 (6)	0.0071 (6)
C19	0.0492 (11)	0.0518 (12)	0.0213 (8)	−0.0005 (9)	0.0022 (7)	0.0043 (7)
C20	0.0393 (10)	0.0578 (13)	0.0318 (9)	0.0094 (9)	0.0116 (7)	0.0013 (8)
C21	0.0245 (7)	0.0424 (10)	0.0307 (8)	0.0063 (7)	0.0017 (6)	0.0051 (7)

Geometric parameters (Å, º) top

N1—N2	1.239 (2)	C9—C10	1.392 (2)
N1—C1	1.4325 (19)	C10—C11	1.390 (2)
N2—N3	1.128 (2)	C10—H10	0.986 (18)
O1—C7	1.2645 (16)	C11—C12	1.389 (2)
O2—C7	1.2554 (17)	C11—H11	0.991 (18)
C7—C4	1.5099 (19)	C12—C13	1.384 (2)
C1—C6	1.386 (2)	C12—H12	0.97 (2)
C1—C2	1.387 (2)	C13—C14	1.386 (2)
C2—C3	1.384 (2)	C13—H13	0.964 (19)
C2—H2	0.968 (19)	C14—H14	0.976 (18)
C3—C4	1.3912 (19)	C15—C16	1.5010 (19)
C3—H3	0.969 (19)	C15—H151	0.991 (17)
C4—C5	1.3911 (19)	C15—H152	0.982 (18)
C5—C6	1.386 (2)	C16—C21	1.389 (2)
C5—H5	0.953 (18)	C16—C17	1.392 (2)
C6—H6	0.963 (19)	C17—C18	1.390 (2)
N4—C8	1.4946 (18)	C17—H17	0.960 (18)
N4—C15	1.4987 (17)	C18—C19	1.381 (3)
N4—H02	0.93 (2)	C18—H18	0.99 (2)
N4—H01	0.97 (2)	C19—C20	1.381 (3)
C8—C9	1.5074 (19)	C19—H19	0.97 (2)
C8—H81	0.960 (18)	C20—C21	1.387 (2)
C8—H82	1.012 (17)	C20—H20	0.98 (2)
C9—C14	1.390 (2)	C21—H21	0.98 (2)

N2—N1—C1	117.44 (13)	C11—C10—H10	120.2 (10)
N3—N2—N1	171.81 (16)	C9—C10—H10	119.8 (11)
O2—C7—O1	124.83 (13)	C12—C11—C10	120.35 (14)
O2—C7—C4	118.89 (12)	C12—C11—H11	120.3 (11)
O1—C7—C4	116.28 (12)	C10—C11—H11	119.3 (11)
C6—C1—C2	120.54 (14)	C13—C12—C11	119.57 (14)
C6—C1—N1	123.17 (14)	C13—C12—H12	119.5 (11)
C2—C1—N1	116.29 (13)	C11—C12—H12	120.9 (11)
C3—C2—C1	119.64 (14)	C12—C13—C14	120.23 (14)
C3—C2—H2	121.5 (11)	C12—C13—H13	120.8 (11)
C1—C2—H2	118.8 (11)	C14—C13—H13	119.0 (11)
C2—C3—C4	120.78 (14)	C13—C14—C9	120.50 (14)
C2—C3—H3	119.0 (11)	C13—C14—H14	119.5 (11)
C4—C3—H3	120.2 (10)	C9—C14—H14	120.0 (11)
C5—C4—C3	118.64 (13)	N4—C15—C16	113.01 (11)
C5—C4—C7	120.68 (12)	N4—C15—H151	105.8 (10)
C3—C4—C7	120.66 (13)	C16—C15—H151	111.5 (10)
C6—C5—C4	121.18 (13)	N4—C15—H152	105.8 (10)
C6—C5—H5	119.3 (11)	C16—C15—H152	110.9 (10)
C4—C5—H5	119.5 (11)	H151—C15—H152	109.5 (15)
C5—C6—C1	119.16 (14)	C21—C16—C17	119.09 (13)
C5—C6—H6	119.3 (11)	C21—C16—C15	120.13 (13)
C1—C6—H6	121.5 (11)	C17—C16—C15	120.77 (13)
C8—N4—C15	113.98 (11)	C18—C17—C16	120.27 (14)
C8—N4—H02	109.7 (12)	C18—C17—H17	119.9 (10)
C15—N4—H02	110.8 (12)	C16—C17—H17	119.9 (10)
C8—N4—H01	110.0 (12)	C19—C18—C17	120.13 (15)
C15—N4—H01	104.5 (12)	C19—C18—H18	121.7 (11)
H02—N4—H01	107.6 (16)	C17—C18—H18	118.1 (11)
N4—C8—C9	109.51 (11)	C20—C19—C18	119.89 (15)
N4—C8—H81	106.0 (11)	C20—C19—H19	120.4 (13)
C9—C8—H81	112.1 (11)	C18—C19—H19	119.7 (13)
N4—C8—H82	108.2 (10)	C19—C20—C21	120.24 (16)
C9—C8—H82	111.2 (10)	C19—C20—H20	120.6 (13)
H81—C8—H82	109.7 (14)	C21—C20—H20	119.2 (13)
C14—C9—C10	119.30 (13)	C20—C21—C16	120.36 (15)
C14—C9—C8	120.04 (13)	C20—C21—H21	120.0 (11)
C10—C9—C8	120.62 (13)	C16—C21—H21	119.7 (11)
C11—C10—C9	120.04 (14)

C1—N1—N2—N3	176.3 (14)	C14—C9—C10—C11	0.1 (2)
N2—N1—C1—C6	12.1 (3)	C8—C9—C10—C11	178.00 (13)
N2—N1—C1—C2	−168.04 (16)	C9—C10—C11—C12	−0.2 (2)
C6—C1—C2—C3	−1.6 (3)	C10—C11—C12—C13	−0.3 (2)
N1—C1—C2—C3	178.49 (16)	C11—C12—C13—C14	0.9 (2)
C1—C2—C3—C4	−0.4 (3)	C12—C13—C14—C9	−0.9 (2)
C2—C3—C4—C5	1.2 (2)	C10—C9—C14—C13	0.4 (2)
C2—C3—C4—C7	−179.83 (14)	C8—C9—C14—C13	−177.46 (13)
O2—C7—C4—C5	173.03 (13)	C8—N4—C15—C16	73.63 (15)
O1—C7—C4—C5	−7.41 (19)	N4—C15—C16—C21	−98.90 (16)
O2—C7—C4—C3	−5.9 (2)	N4—C15—C16—C17	80.42 (17)
O1—C7—C4—C3	173.64 (13)	C21—C16—C17—C18	1.3 (2)
C3—C4—C5—C6	0.0 (2)	C15—C16—C17—C18	−178.04 (14)
C7—C4—C5—C6	−178.93 (13)	C16—C17—C18—C19	−0.3 (3)
C4—C5—C6—C1	−2.0 (2)	C17—C18—C19—C20	−0.8 (3)
C2—C1—C6—C5	2.8 (2)	C18—C19—C20—C21	0.9 (3)
N1—C1—C6—C5	−177.29 (15)	C19—C20—C21—C16	0.1 (3)
C15—N4—C8—C9	−179.16 (11)	C17—C16—C21—C20	−1.2 (3)
N4—C8—C9—C14	94.56 (15)	C15—C16—C21—C20	178.14 (17)
N4—C8—C9—C10	−83.30 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H01···O1ⁱ	0.97 (2)	1.68 (2)	2.6384 (15)	170.0 (19)
N4—H02···O2	0.93 (2)	1.86 (2)	2.7736 (15)	171.5 (17)

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

Dicyclohexylammonium 4-azidebenzoate (4a-dc-i) top

Crystal data top

C₁₉H₂₈N₄O₂	Z = 2
M_r = 344.45	F(000) = 372
Triclinic, p1	D_x = 1.234 Mg m⁻³
a = 9.0015 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3009 (2) Å	Cell parameters from 8192 reflections
c = 11.8819 (1) Å	µ = 0.08 mm⁻¹
α = 107.909 (1)°	T = 80 K
β = 100.454 (1)°	Plate, pale-yellow
γ = 91.613 (1)°	0.23 × 0.18 × 0.16 mm
V = 927.11 (3) Å³

Data collection top

Bruker SMART CCD area detector system diffractometer	5369 independent reflections
Radiation source: rotating anode	4476 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 30.0°, θ_min = 1.8°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −12→12
T_min = 0.981, T_max = 0.987	k = −13→13
14876 measured reflections	l = −16→16

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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0705P)²] where P = (F_o² + 2F_c²)/3
5369 reflections	(Δ/σ)_max < 0.001
306 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C7	0.34728 (9)	0.23018 (9)	−0.21129 (7)	0.01336 (15)
C4	0.27903 (9)	0.09543 (8)	−0.32075 (7)	0.01275 (15)
C3	0.32593 (10)	0.07436 (10)	−0.43020 (7)	0.01852 (17)
H3	0.4041 (13)	0.1445 (13)	−0.4340 (11)	0.022*
C2	0.26616 (11)	−0.04998 (10)	−0.53101 (8)	0.02156 (18)
H2	0.3003 (13)	−0.0659 (14)	−0.6067 (11)	0.026*
C1	0.15619 (10)	−0.15322 (9)	−0.52292 (7)	0.01729 (16)
C6	0.10717 (9)	−0.13356 (9)	−0.41448 (7)	0.01653 (16)
H6	0.0270 (13)	−0.2037 (13)	−0.4082 (10)	0.020*
C5	0.16986 (9)	−0.00971 (9)	−0.31390 (7)	0.01507 (16)
H5	0.1354 (12)	0.0026 (12)	−0.2382 (10)	0.018*
N1	0.10055 (10)	−0.27766 (9)	−0.63098 (7)	0.02580 (18)
N2	0.00167 (9)	−0.36899 (9)	−0.62448 (7)	0.02437 (18)
N3	−0.08790 (10)	−0.46096 (10)	−0.63058 (9)	0.0354 (2)
O1	0.32736 (7)	0.22575 (7)	−0.10966 (5)	0.01705 (13)
O2	0.42010 (7)	0.33600 (7)	−0.22984 (6)	0.01876 (14)
C8	0.44971 (8)	0.29984 (8)	0.18519 (7)	0.01120 (14)
H8	0.4349 (12)	0.1877 (12)	0.1484 (10)	0.013*
C9	0.29221 (9)	0.35908 (9)	0.18393 (7)	0.01391 (15)
H91	0.2323 (12)	0.3301 (12)	0.0999 (10)	0.017*
H92	0.3026 (12)	0.4755 (12)	0.2132 (10)	0.017*
C10	0.20808 (9)	0.29855 (9)	0.26378 (7)	0.01592 (16)
H101	0.1039 (13)	0.3382 (13)	0.2618 (10)	0.019*
H102	0.1903 (13)	0.1838 (13)	0.2295 (10)	0.019*
C11	0.30000 (10)	0.34268 (10)	0.39316 (7)	0.01749 (16)
H111	0.2448 (13)	0.3015 (13)	0.4441 (11)	0.021*
H112	0.3116 (13)	0.4565 (13)	0.4299 (11)	0.021*
C12	0.45846 (9)	0.28592 (10)	0.39391 (7)	0.01726 (16)
H121	0.4480 (12)	0.1717 (13)	0.3650 (10)	0.021*
H122	0.5167 (13)	0.3181 (13)	0.4755 (11)	0.021*
C13	0.54395 (9)	0.34401 (9)	0.31363 (7)	0.01437 (15)
H131	0.5652 (12)	0.4570 (13)	0.3473 (10)	0.017*
H132	0.6433 (12)	0.3005 (12)	0.3144 (10)	0.017*
C14	0.67994 (8)	0.30815 (8)	0.08581 (7)	0.01092 (14)
H14	0.7508 (12)	0.3448 (12)	0.1652 (10)	0.013*
C15	0.67317 (8)	0.13498 (8)	0.03705 (7)	0.01300 (15)
H151	0.5903 (12)	0.0958 (12)	−0.0378 (10)	0.016*
H152	0.6472 (12)	0.0881 (12)	0.0954 (10)	0.016*
C16	0.82612 (9)	0.08478 (9)	0.00644 (7)	0.01521 (16)
H161	0.9051	0.1157	0.0812	0.018*
H162	0.8188	−0.0272	−0.0277	0.018*
C17	0.87218 (10)	0.15505 (10)	−0.08433 (8)	0.01899 (17)
H171	0.9702 (13)	0.1202 (13)	−0.1059 (11)	0.023*
H172	0.7954 (14)	0.1184 (13)	−0.1600 (11)	0.023*
C18	0.88202 (9)	0.32790 (10)	−0.03397 (8)	0.01720 (16)
H181	0.9058 (13)	0.3722 (13)	−0.0929 (11)	0.021*
H182	0.9633 (13)	0.3644 (13)	0.0399 (11)	0.021*
C19	0.73172 (9)	0.38297 (9)	−0.00087 (7)	0.01373 (15)
H191	0.6521 (12)	0.3556 (12)	−0.0753 (10)	0.016*
H192	0.7395 (12)	0.4920 (13)	0.0339 (10)	0.016*
N4	0.52640 (7)	0.36044 (7)	0.10448 (6)	0.01064 (13)
H01	0.4593 (14)	0.3316 (14)	0.0283 (12)	0.025 (3)*
H02	0.5355 (14)	0.4614 (14)	0.1341 (11)	0.026 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.0140 (3)	0.0112 (3)	0.0129 (3)	0.0016 (3)	0.0004 (3)	0.0023 (3)
C4	0.0152 (3)	0.0107 (3)	0.0111 (3)	0.0007 (3)	0.0006 (3)	0.0028 (3)
C3	0.0242 (4)	0.0171 (4)	0.0136 (4)	−0.0048 (3)	0.0036 (3)	0.0046 (3)
C2	0.0297 (5)	0.0212 (4)	0.0119 (4)	−0.0040 (3)	0.0060 (3)	0.0020 (3)
C1	0.0201 (4)	0.0150 (4)	0.0121 (3)	−0.0006 (3)	0.0002 (3)	−0.0004 (3)
C6	0.0163 (4)	0.0149 (4)	0.0159 (4)	−0.0025 (3)	0.0029 (3)	0.0018 (3)
C5	0.0158 (3)	0.0151 (4)	0.0128 (3)	−0.0004 (3)	0.0034 (3)	0.0021 (3)
N1	0.0304 (4)	0.0228 (4)	0.0158 (3)	−0.0068 (3)	0.0036 (3)	−0.0044 (3)
N2	0.0207 (4)	0.0212 (4)	0.0199 (4)	−0.0004 (3)	0.0010 (3)	−0.0076 (3)
N3	0.0269 (4)	0.0282 (4)	0.0355 (5)	−0.0097 (3)	0.0072 (4)	−0.0116 (4)
O1	0.0199 (3)	0.0176 (3)	0.0108 (3)	−0.0017 (2)	0.0011 (2)	0.0019 (2)
O2	0.0246 (3)	0.0116 (3)	0.0180 (3)	−0.0034 (2)	0.0028 (2)	0.0029 (2)
C8	0.0121 (3)	0.0111 (3)	0.0109 (3)	0.0001 (2)	0.0034 (2)	0.0035 (3)
C9	0.0121 (3)	0.0168 (4)	0.0133 (3)	0.0021 (3)	0.0032 (3)	0.0051 (3)
C10	0.0134 (3)	0.0189 (4)	0.0151 (4)	0.0001 (3)	0.0053 (3)	0.0035 (3)
C11	0.0189 (4)	0.0205 (4)	0.0134 (4)	−0.0012 (3)	0.0062 (3)	0.0045 (3)
C12	0.0176 (4)	0.0215 (4)	0.0142 (4)	−0.0012 (3)	0.0027 (3)	0.0085 (3)
C13	0.0134 (3)	0.0180 (4)	0.0121 (3)	−0.0015 (3)	0.0012 (3)	0.0063 (3)
C14	0.0100 (3)	0.0109 (3)	0.0116 (3)	0.0008 (2)	0.0027 (2)	0.0029 (3)
C15	0.0129 (3)	0.0106 (3)	0.0153 (3)	0.0007 (3)	0.0027 (3)	0.0039 (3)
C16	0.0159 (3)	0.0133 (3)	0.0177 (4)	0.0041 (3)	0.0060 (3)	0.0049 (3)
C17	0.0217 (4)	0.0197 (4)	0.0194 (4)	0.0079 (3)	0.0109 (3)	0.0074 (3)
C18	0.0153 (4)	0.0191 (4)	0.0213 (4)	0.0025 (3)	0.0080 (3)	0.0098 (3)
C19	0.0142 (3)	0.0127 (3)	0.0162 (3)	0.0015 (3)	0.0051 (3)	0.0061 (3)
N4	0.0112 (3)	0.0103 (3)	0.0104 (3)	0.0007 (2)	0.0027 (2)	0.0030 (2)

Geometric parameters (Å, º) top

C7—O2	1.2635 (9)	C11—H111	1.000 (12)
C7—O1	1.2652 (10)	C11—H112	1.008 (12)
C7—C4	1.5179 (11)	C12—C13	1.5341 (11)
C4—C5	1.3973 (11)	C12—H121	1.007 (11)
C4—C3	1.3983 (11)	C12—H122	0.966 (12)
C3—C2	1.3931 (12)	C13—H131	1.002 (11)
C3—H3	0.962 (11)	C13—H132	0.992 (11)
C2—C1	1.3961 (12)	C14—N4	1.5095 (9)
C2—H2	0.973 (12)	C14—C15	1.5301 (10)
C1—C6	1.3979 (12)	C14—C19	1.5358 (10)
C1—N1	1.4349 (11)	C14—H14	0.992 (11)
C6—C5	1.3948 (11)	C15—C16	1.5360 (10)
C6—H6	0.987 (11)	C15—H151	1.012 (11)
C5—H5	0.979 (11)	C15—H152	0.982 (11)
N1—N2	1.2420 (11)	C16—C17	1.5307 (11)
N2—N3	1.1352 (12)	C16—H161	0.9900
C8—N4	1.5048 (9)	C16—H162	0.9900
C8—C13	1.5305 (11)	C17—C18	1.5270 (12)
C8—C9	1.5347 (10)	C17—H171	0.998 (12)
C8—H8	0.993 (11)	C17—H172	0.987 (12)
C9—C10	1.5349 (11)	C18—C19	1.5348 (11)
C9—H91	0.996 (11)	C18—H181	0.966 (12)
C9—H92	1.026 (11)	C18—H182	0.995 (12)
C10—C11	1.5322 (11)	C19—H191	0.991 (11)
C10—H101	1.016 (11)	C19—H192	0.966 (11)
C10—H102	1.015 (11)	N4—H01	0.949 (13)
C11—C12	1.5343 (12)	N4—H02	0.892 (13)

O2—C7—O1	125.91 (7)	C13—C12—H122	109.4 (7)
O2—C7—C4	117.00 (7)	H121—C12—H122	107.1 (9)
O1—C7—C4	117.09 (7)	C8—C13—C12	109.97 (6)
C5—C4—C3	119.00 (7)	C8—C13—H131	109.8 (6)
C5—C4—C7	120.91 (7)	C12—C13—H131	110.1 (6)
C3—C4—C7	120.09 (7)	C8—C13—H132	111.1 (6)
C2—C3—C4	120.82 (8)	C12—C13—H132	108.8 (6)
C2—C3—H3	120.2 (7)	H131—C13—H132	107.1 (9)
C4—C3—H3	118.9 (7)	N4—C14—C15	111.21 (6)
C3—C2—C1	119.44 (8)	N4—C14—C19	107.16 (6)
C3—C2—H2	120.9 (7)	C15—C14—C19	111.95 (6)
C1—C2—H2	119.7 (7)	N4—C14—H14	107.7 (6)
C2—C1—C6	120.56 (7)	C15—C14—H14	109.2 (6)
C2—C1—N1	115.78 (8)	C19—C14—H14	109.5 (6)
C6—C1—N1	123.66 (8)	C14—C15—C16	110.36 (6)
C5—C6—C1	119.26 (7)	C14—C15—H151	109.6 (6)
C5—C6—H6	119.3 (7)	C16—C15—H151	109.7 (6)
C1—C6—H6	121.5 (7)	C14—C15—H152	111.5 (6)
C6—C5—C4	120.91 (7)	C16—C15—H152	109.1 (6)
C6—C5—H5	118.7 (6)	H151—C15—H152	106.4 (9)
C4—C5—H5	120.4 (6)	C17—C16—C15	111.27 (6)
N2—N1—C1	115.97 (8)	C17—C16—H161	109.4
N3—N2—N1	172.81 (9)	C15—C16—H161	109.4
N4—C8—C13	111.79 (6)	C17—C16—H162	109.4
N4—C8—C9	108.21 (6)	C15—C16—H162	109.4
C13—C8—C9	111.42 (6)	H161—C16—H162	108.0
N4—C8—H8	107.0 (6)	C18—C17—C16	110.20 (7)
C13—C8—H8	110.6 (6)	C18—C17—H171	110.8 (7)
C9—C8—H8	107.6 (6)	C16—C17—H171	111.3 (7)
C8—C9—C10	110.30 (6)	C18—C17—H172	110.1 (7)
C8—C9—H91	110.6 (6)	C16—C17—H172	108.4 (7)
C10—C9—H91	110.7 (6)	H171—C17—H172	106.0 (9)
C8—C9—H92	109.9 (6)	C17—C18—C19	111.29 (6)
C10—C9—H92	110.5 (6)	C17—C18—H181	110.2 (7)
H91—C9—H92	104.7 (8)	C19—C18—H181	108.4 (7)
C11—C10—C9	110.87 (6)	C17—C18—H182	109.7 (7)
C11—C10—H101	111.3 (7)	C19—C18—H182	108.5 (7)
C9—C10—H101	109.5 (6)	H181—C18—H182	108.7 (9)
C11—C10—H102	109.1 (6)	C18—C19—C14	111.59 (6)
C9—C10—H102	109.6 (6)	C18—C19—H191	109.0 (6)
H101—C10—H102	106.4 (9)	C14—C19—H191	107.8 (6)
C10—C11—C12	110.47 (7)	C18—C19—H192	111.1 (7)
C10—C11—H111	110.2 (7)	C14—C19—H192	110.1 (7)
C12—C11—H111	111.0 (7)	H191—C19—H192	107.0 (9)
C10—C11—H112	109.5 (7)	C8—N4—C14	117.35 (6)
C12—C11—H112	108.6 (6)	C8—N4—H01	106.3 (7)
H111—C11—H112	107.0 (9)	C14—N4—H01	108.4 (7)
C11—C12—C13	112.03 (7)	C8—N4—H02	108.0 (8)
C11—C12—H121	108.9 (6)	C14—N4—H02	108.4 (8)
C13—C12—H121	109.6 (7)	H01—N4—H02	108.0 (11)
C11—C12—H122	109.7 (7)

O2—C7—C4—C5	−165.63 (7)	C8—C9—C10—C11	57.14 (9)
O1—C7—C4—C5	15.02 (11)	C9—C10—C11—C12	−56.24 (9)
O2—C7—C4—C3	14.85 (11)	C10—C11—C12—C13	55.91 (9)
O1—C7—C4—C3	−164.50 (7)	N4—C8—C13—C12	177.54 (6)
C5—C4—C3—C2	−0.53 (13)	C9—C8—C13—C12	56.33 (8)
C7—C4—C3—C2	179.00 (8)	C11—C12—C13—C8	−55.67 (9)
C4—C3—C2—C1	1.11 (14)	N4—C14—C15—C16	174.20 (6)
C3—C2—C1—C6	−0.70 (14)	C19—C14—C15—C16	54.36 (8)
C3—C2—C1—N1	179.85 (8)	C14—C15—C16—C17	−56.99 (8)
C2—C1—C6—C5	−0.27 (13)	C15—C16—C17—C18	58.26 (9)
N1—C1—C6—C5	179.13 (8)	C16—C17—C18—C19	−56.65 (9)
C1—C6—C5—C4	0.86 (13)	C17—C18—C19—C14	54.45 (9)
C3—C4—C5—C6	−0.46 (12)	N4—C14—C19—C18	−175.65 (6)
C7—C4—C5—C6	−179.99 (7)	C15—C14—C19—C18	−53.46 (8)
C2—C1—N1—N2	−179.36 (9)	C13—C8—N4—C14	60.74 (8)
C6—C1—N1—N2	1.21 (14)	C9—C8—N4—C14	−176.20 (6)
C1—N1—N2—N3	−176.4 (8)	C15—C14—N4—C8	56.33 (8)
N4—C8—C9—C10	179.22 (6)	C19—C14—N4—C8	178.98 (6)
C13—C8—C9—C10	−57.50 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H01···O1	0.949 (13)	1.817 (13)	2.7409 (9)	163.9 (11)
N4—H02···O2ⁱ	0.892 (13)	1.865 (13)	2.7384 (9)	166.0 (12)

Symmetry code: (i) −x+1, −y+1, −z.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text