Conformational polymorphism of 3-(azido­meth­yl)benzoic acid

Three conformational polymorphs of 3-(azido­meth­yl)benzoic acid, C₈H₇N₃O₂, are reported. All three structures maintain similar carb­oxy­lic acid dimers and π–π stacking. Crystal structure analysis and com­putational evaluations highlight the azido­methyl group as a source of conformational polymorphism, thus having potential implications in the design of solid-state reactions.

Computing details

For all structures, data collection: APEX4 (Bruker, 2021); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016). Program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a) for A, C; SHELXT2018 (Sheldrick, 2015a) and SHELXS (Sheldrick, 2008) for B. For all structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-(Azidomethyl)benzoic acid (A)

Crystal data

C8H7N3O2	F(000) = 368
Mr = 177.17	Dx = 1.473 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.6327 (5) Å	Cell parameters from 7334 reflections
b = 9.5561 (6) Å	θ = 2.8–28.0°
c = 11.2899 (7) Å	µ = 0.11 mm^−1
β = 104.095 (3)°	T = 100 K
V = 798.68 (9) Å^3	Plate, colourless
Z = 4	0.16 × 0.12 × 0.04 mm

Data collection

Bruker D8 VENTURE DUO diffractometer	1988 independent reflections
Radiation source: sealed tube, fine-focus	1496 reflections with I > 2σ(I)
TRIUMPH graphite monochromator	Rint = 0.059
Detector resolution: 7.39 pixels mm^-1	θmax = 28.4°, θmin = 2.8°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −12→12
Tmin = 0.675, Tmax = 0.746	l = −15→15
21950 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0404P)^2 + 0.4603P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1988 reflections	Δρmax = 0.32 e Å^−3
122 parameters	Δρmin = −0.23 e Å^−3
0 restraints

Special details

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

Refinement. Data for all structures were collected at 100 K on a Bruker D8 VENTURE Duo fixed-chi three-circle diffractometer using Mo Kα radiation (λ = 0.71073 Å). All data were integrated with SAINT (Bruker, 2016) and corrected for absorption using SADABS (Krause et al., 2015). The structures of polymorphs A and C were solved by dual methods using SHELXT (Sheldrick, 2015a), while B was solved by direct methods using SHELXS (Sheldrick, 2008). All structures were refined by full-matrix least-squares methods against F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined with anisotropic displacement parameters.

Calculations and refinement of the structure was carried out using APEX4 (Bruker, 2021) and OLEX2 (Dolomanov et al., 2009) software. Crystal packing diagrams were generated using OLEX2. Structure overlay diagrams and r.m.s. deviation values were obtained using Mercury (Macrae et al., 2020). For polymorph B, the TWINROTMAT routine within PLATON (Spek, 2020) indicated twinning. The twin law was found to be (100, 010, 101). The BASF value refined to 0.5471 (16).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.93737 (15)	0.86449 (11)	0.40596 (9)	0.0215 (3)
O2	0.90744 (16)	0.88984 (12)	0.59702 (9)	0.0220 (3)
H2	0.962 (4)	0.979 (3)	0.591 (2)	0.083 (9)*
N1	0.56587 (18)	0.34979 (13)	0.20286 (11)	0.0219 (3)
N2	0.50663 (18)	0.46363 (14)	0.15900 (11)	0.0208 (3)
N3	0.4361 (2)	0.56102 (16)	0.11360 (13)	0.0306 (3)
C1	0.82040 (18)	0.67382 (14)	0.49777 (12)	0.0137 (3)
C2	0.81239 (18)	0.58766 (14)	0.39627 (12)	0.0137 (3)
H2A	0.845507	0.623981	0.326465	0.016*
C3	0.75637 (18)	0.44948 (15)	0.39698 (12)	0.0140 (3)
C4	0.70877 (19)	0.39726 (15)	0.50081 (13)	0.0159 (3)
H4	0.671218	0.302652	0.502454	0.019*
C5	0.71607 (19)	0.48268 (15)	0.60125 (13)	0.0172 (3)
H5	0.683240	0.446267	0.671121	0.021*
C6	0.77106 (19)	0.62109 (15)	0.60026 (12)	0.0159 (3)
H6	0.775077	0.679528	0.668945	0.019*
C7	0.89182 (19)	0.81756 (15)	0.49687 (12)	0.0152 (3)
C8	0.74914 (19)	0.35650 (15)	0.28813 (12)	0.0172 (3)
H8A	0.836393	0.391527	0.243022	0.021*
H8B	0.786820	0.260833	0.317165	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0348 (6)	0.0163 (5)	0.0164 (5)	−0.0041 (5)	0.0122 (5)	0.0002 (4)
O2	0.0371 (6)	0.0158 (5)	0.0147 (5)	−0.0060 (5)	0.0096 (4)	−0.0044 (4)
N1	0.0297 (7)	0.0152 (6)	0.0181 (6)	−0.0009 (5)	0.0005 (5)	−0.0018 (5)
N2	0.0271 (7)	0.0236 (7)	0.0119 (6)	0.0010 (6)	0.0055 (5)	−0.0040 (5)
N3	0.0404 (9)	0.0292 (8)	0.0226 (7)	0.0117 (7)	0.0081 (6)	0.0035 (6)
C1	0.0150 (6)	0.0132 (6)	0.0126 (6)	0.0006 (5)	0.0028 (5)	0.0012 (5)
C2	0.0143 (6)	0.0153 (7)	0.0117 (6)	0.0005 (5)	0.0039 (5)	0.0019 (5)
C3	0.0137 (6)	0.0144 (7)	0.0138 (6)	0.0016 (5)	0.0030 (5)	−0.0005 (5)
C4	0.0157 (7)	0.0136 (7)	0.0186 (7)	−0.0013 (5)	0.0046 (5)	0.0024 (5)
C5	0.0190 (7)	0.0203 (7)	0.0137 (6)	0.0000 (6)	0.0067 (6)	0.0030 (6)
C6	0.0177 (7)	0.0183 (7)	0.0119 (6)	0.0008 (6)	0.0042 (5)	−0.0010 (5)
C7	0.0176 (7)	0.0153 (7)	0.0121 (6)	0.0010 (5)	0.0028 (5)	−0.0003 (5)
C8	0.0217 (7)	0.0154 (7)	0.0150 (6)	−0.0002 (6)	0.0055 (6)	−0.0017 (5)

Geometric parameters (Å, º)

O1—C7	1.2446 (17)	C2—C3	1.389 (2)
O2—H2	0.96 (3)	C3—C4	1.4010 (19)
O2—C7	1.3054 (17)	C3—C8	1.5065 (19)
N1—N2	1.2345 (18)	C4—H4	0.9500
N1—C8	1.4939 (19)	C4—C5	1.387 (2)
N2—N3	1.1333 (19)	C5—H5	0.9500
C1—C2	1.4002 (19)	C5—C6	1.389 (2)
C1—C6	1.3953 (19)	C6—H6	0.9500
C1—C7	1.479 (2)	C8—H8A	0.9900
C2—H2A	0.9500	C8—H8B	0.9900
C7—O2—H2	111.0 (17)	C4—C5—H5	119.8
N2—N1—C8	114.49 (12)	C4—C5—C6	120.40 (13)
N3—N2—N1	172.89 (16)	C6—C5—H5	119.8
C2—C1—C7	118.90 (12)	C1—C6—H6	120.2
C6—C1—C2	119.97 (13)	C5—C6—C1	119.59 (13)
C6—C1—C7	121.03 (12)	C5—C6—H6	120.2
C1—C2—H2A	119.8	O1—C7—O2	122.59 (13)
C3—C2—C1	120.44 (12)	O1—C7—C1	121.19 (12)
C3—C2—H2A	119.8	O2—C7—C1	116.21 (12)
C2—C3—C4	119.11 (12)	N1—C8—C3	113.18 (12)
C2—C3—C8	120.42 (12)	N1—C8—H8A	108.9
C4—C3—C8	120.46 (12)	N1—C8—H8B	108.9
C3—C4—H4	119.8	C3—C8—H8A	108.9
C5—C4—C3	120.49 (13)	C3—C8—H8B	108.9
C5—C4—H4	119.8	H8A—C8—H8B	107.8
N2—N1—C8—C3	59.97 (17)	C4—C3—C8—N1	85.04 (16)
C1—C2—C3—C4	−0.3 (2)	C4—C5—C6—C1	−0.5 (2)
C1—C2—C3—C8	−179.53 (12)	C6—C1—C2—C3	−0.3 (2)
C2—C1—C6—C5	0.7 (2)	C6—C1—C7—O1	179.39 (13)
C2—C1—C7—O1	3.0 (2)	C6—C1—C7—O2	0.8 (2)
C2—C1—C7—O2	−175.56 (13)	C7—C1—C2—C3	176.11 (12)
C2—C3—C4—C5	0.5 (2)	C7—C1—C6—C5	−175.65 (13)
C2—C3—C8—N1	−95.73 (15)	C8—C3—C4—C5	179.75 (13)
C3—C4—C5—C6	−0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.96 (3)	1.68 (3)	2.6334 (15)	175 (3)

Symmetry code: (i) −x+2, −y+2, −z+1.

3-(Azidomethyl)benzoic acid (B)

Crystal data

C8H7N3O2	F(000) = 368
Mr = 177.17	Dx = 1.464 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.7712 (3) Å	Cell parameters from 5546 reflections
b = 6.1229 (5) Å	θ = 3.4–26.2°
c = 34.868 (3) Å	µ = 0.11 mm^−1
β = 93.099 (3)°	T = 100 K
V = 803.96 (11) Å^3	Plate, colourless
Z = 4	0.28 × 0.06 × 0.02 mm

Data collection

Bruker D8 VENTURE DUO diffractometer	1656 independent reflections
Radiation source: sealed tube, fine-focus	1411 reflections with I > 2σ(I)
TRIUMPH graphite monochromator	Rint = 0.036
Detector resolution: 7.39 pixels mm^-1	θmax = 26.4°, θmin = 2.9°
ω and φ scans	h = −4→4
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −7→7
Tmin = 0.682, Tmax = 0.745	l = −43→43
10613 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0299P)^2 + 0.3387P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
1656 reflections	Δρmax = 0.25 e Å^−3
123 parameters	Δρmin = −0.23 e Å^−3
0 restraints

Special details

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

Refinement. Refined as a 2-component twin.

Data for all structures were collected at 100 K on a Bruker D8 VENTURE Duo fixed-chi three-circle diffractometer using Mo Kα radiation (λ = 0.71073 Å). All data were integrated with SAINT (Bruker, 2016) and corrected for absorption using SADABS (Krause et al., 2015). The structures of polymorphs A and C were solved by dual methods using SHELXT (Sheldrick, 2015a), while B was solved by direct methods using SHELXS (Sheldrick, 2008). All structures were refined by full-matrix least-squares methods against F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined with anisotropic displacement parameters.

Calculations and refinement of the structure was carried out using APEX4 (Bruker, 2021) and OLEX2 (Dolomanov et al., 2009) software. Crystal packing diagrams were generated using OLEX2. Structure overlay diagrams and r.m.s. deviation values were obtained using Mercury (Macrae et al., 2020). For polymorph B, the TWINROTMAT routine within PLATON (Spek, 2020) indicated twinning. The twin law was found to be (100, 010, 101). The BASF value refined to 0.5471 (16).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.0623 (4)	0.4961 (2)	0.04746 (4)	0.0214 (4)
O2	0.7725 (4)	0.2518 (3)	0.00956 (4)	0.0243 (4)
H1	0.832 (9)	0.347 (5)	−0.0081 (9)	0.072 (11)*
N1	0.7854 (5)	0.4340 (3)	0.19050 (5)	0.0249 (5)
N2	0.9692 (6)	0.5552 (3)	0.21177 (5)	0.0232 (5)
N3	1.1081 (7)	0.6857 (3)	0.22997 (6)	0.0362 (6)
C1	0.8065 (6)	0.1853 (3)	0.07635 (6)	0.0160 (5)
C2	0.8930 (5)	0.2600 (3)	0.11338 (5)	0.0161 (5)
H2	1.002494	0.398639	0.117123	0.019*
C3	0.8194 (6)	0.1319 (3)	0.14487 (6)	0.0156 (5)
C4	0.6584 (6)	−0.0703 (3)	0.13902 (6)	0.0178 (5)
H4	0.604339	−0.157416	0.160482	0.021*
C5	0.5758 (6)	−0.1466 (3)	0.10202 (6)	0.0192 (5)
H5	0.469034	−0.286048	0.098269	0.023*
C6	0.6495 (6)	−0.0188 (3)	0.07071 (6)	0.0173 (5)
H6	0.593077	−0.070155	0.045407	0.021*
C7	0.8919 (6)	0.3249 (3)	0.04313 (6)	0.0165 (5)
C8	0.9242 (6)	0.2094 (3)	0.18508 (6)	0.0194 (5)
H8A	0.825573	0.109447	0.204114	0.023*
H8B	1.186115	0.209188	0.189068	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0269 (9)	0.0196 (8)	0.0177 (7)	−0.0068 (8)	0.0005 (7)	−0.0012 (6)
O2	0.0336 (10)	0.0257 (9)	0.0132 (8)	−0.0101 (9)	−0.0031 (7)	0.0002 (7)
N1	0.0306 (13)	0.0214 (10)	0.0217 (9)	0.0026 (10)	−0.0081 (9)	−0.0047 (8)
N2	0.0318 (12)	0.0240 (10)	0.0134 (9)	0.0075 (10)	−0.0018 (9)	0.0018 (9)
N3	0.0509 (15)	0.0262 (11)	0.0299 (11)	0.0041 (12)	−0.0112 (11)	−0.0117 (10)
C1	0.0133 (11)	0.0180 (11)	0.0167 (10)	0.0027 (10)	−0.0006 (10)	0.0005 (8)
C2	0.0156 (12)	0.0134 (11)	0.0191 (11)	−0.0004 (10)	−0.0011 (9)	−0.0022 (8)
C3	0.0123 (12)	0.0174 (11)	0.0168 (11)	0.0034 (10)	−0.0020 (9)	−0.0006 (8)
C4	0.0146 (12)	0.0182 (11)	0.0208 (11)	0.0019 (10)	0.0023 (9)	0.0043 (9)
C5	0.0164 (12)	0.0138 (11)	0.0270 (12)	−0.0016 (11)	−0.0031 (10)	−0.0020 (9)
C6	0.0148 (12)	0.0195 (11)	0.0174 (10)	0.0019 (10)	−0.0007 (9)	−0.0027 (9)
C7	0.0165 (12)	0.0179 (11)	0.0151 (10)	0.0047 (11)	0.0008 (9)	−0.0033 (8)
C8	0.0218 (13)	0.0171 (11)	0.0189 (11)	0.0015 (11)	−0.0015 (9)	0.0009 (8)

Geometric parameters (Å, º)

O1—C7	1.235 (3)	C2—C3	1.390 (3)
O2—H1	0.89 (3)	C3—C4	1.389 (3)
O2—C7	1.310 (2)	C3—C8	1.512 (3)
N1—N2	1.235 (3)	C4—H4	0.9500
N1—C8	1.487 (3)	C4—C5	1.391 (3)
N2—N3	1.131 (3)	C5—H5	0.9500
C1—C2	1.392 (3)	C5—C6	1.384 (3)
C1—C6	1.392 (3)	C6—H6	0.9500
C1—C7	1.489 (3)	C8—H8A	0.9900
C2—H2	0.9500	C8—H8B	0.9900
C7—O2—H1	108.0 (19)	C4—C5—H5	120.1
N2—N1—C8	116.23 (18)	C6—C5—C4	119.8 (2)
N3—N2—N1	171.5 (2)	C6—C5—H5	120.1
C2—C1—C7	118.89 (19)	C1—C6—H6	120.1
C6—C1—C2	120.19 (19)	C5—C6—C1	119.89 (19)
C6—C1—C7	120.91 (18)	C5—C6—H6	120.1
C1—C2—H2	120.0	O1—C7—O2	123.42 (18)
C3—C2—C1	120.05 (19)	O1—C7—C1	121.70 (18)
C3—C2—H2	120.0	O2—C7—C1	114.88 (19)
C2—C3—C8	120.15 (18)	N1—C8—C3	109.37 (17)
C4—C3—C2	119.42 (18)	N1—C8—H8A	109.8
C4—C3—C8	120.40 (18)	N1—C8—H8B	109.8
C3—C4—H4	119.7	C3—C8—H8A	109.8
C3—C4—C5	120.64 (19)	C3—C8—H8B	109.8
C5—C4—H4	119.7	H8A—C8—H8B	108.2
N2—N1—C8—C3	−146.9 (2)	C4—C3—C8—N1	−129.8 (2)
C1—C2—C3—C4	−0.1 (3)	C4—C5—C6—C1	0.1 (3)
C1—C2—C3—C8	177.95 (19)	C6—C1—C2—C3	−0.7 (3)
C2—C1—C6—C5	0.7 (3)	C6—C1—C7—O1	−172.7 (2)
C2—C1—C7—O1	5.9 (3)	C6—C1—C7—O2	7.4 (3)
C2—C1—C7—O2	−173.96 (19)	C7—C1—C2—C3	−179.4 (2)
C2—C3—C4—C5	1.0 (3)	C7—C1—C6—C5	179.4 (2)
C2—C3—C8—N1	52.1 (3)	C8—C3—C4—C5	−177.1 (2)
C3—C4—C5—C6	−0.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1^i	0.89 (3)	1.74 (3)	2.619 (2)	172 (3)

Symmetry code: (i) −x+2, −y+1, −z.

3-(Azidomethyl)benzoic acid (C)

Crystal data

C8H7N3O2	Z = 2
Mr = 177.17	F(000) = 184
Triclinic, P1	Dx = 1.486 Mg m^−3
a = 3.8029 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9199 (5) Å	Cell parameters from 4919 reflections
c = 11.5709 (6) Å	θ = 3.5–25.0°
α = 66.828 (2)°	µ = 0.11 mm^−1
β = 82.168 (3)°	T = 100 K
γ = 82.245 (2)°	Plate, colourless
V = 395.96 (4) Å^3	0.31 × 0.12 × 0.01 mm

Data collection

Bruker D8 VENTURE DUO diffractometer	1405 independent reflections
Radiation source: sealed tube, fine-focus	1196 reflections with I > 2σ(I)
TRIUMPH graphite monochromator	Rint = 0.039
Detector resolution: 7.39 pixels mm^-1	θmax = 25.1°, θmin = 2.3°
ω and φ scans	h = −4→4
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −11→11
Tmin = 0.692, Tmax = 0.745	l = −13→13
10604 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.186P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1405 reflections	Δρmax = 0.28 e Å^−3
122 parameters	Δρmin = −0.22 e Å^−3
0 restraints

Special details

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

Refinement. Data for all structures were collected at 100 K on a Bruker D8 VENTURE Duo fixed-chi three-circle diffractometer using Mo Kα radiation (λ = 0.71073 Å). All data were integrated with SAINT (Bruker, 2016) and corrected for absorption using SADABS (Krause et al., 2015). The structures of polymorphs A and C were solved by dual methods using SHELXT (Sheldrick, 2015a), while B was solved by direct methods using SHELXS (Sheldrick, 2008). All structures were refined by full-matrix least-squares methods against F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined with anisotropic displacement parameters.

Calculations and refinement of the structure was carried out using APEX4 (Bruker, 2021) and OLEX2 (Dolomanov et al., 2009) software. Crystal packing diagrams were generated using OLEX2. Structure overlay diagrams and r.m.s. deviation values were obtained using Mercury (Macrae et al., 2020). For polymorph B, the TWINROTMAT routine within PLATON (Spek, 2020) indicated twinning. The twin law was found to be (100, 010, 101). The BASF value refined to 0.5471 (16).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0326 (3)	0.83827 (12)	0.49082 (10)	0.0198 (3)
O2	0.2904 (3)	1.03789 (12)	0.35458 (11)	0.0227 (3)
H2	0.186 (6)	1.078 (3)	0.410 (2)	0.054 (7)*
N1	0.3359 (4)	0.40072 (15)	0.21257 (14)	0.0251 (4)
N2	0.5625 (4)	0.33494 (15)	0.16159 (13)	0.0221 (3)
N3	0.7443 (4)	0.27491 (18)	0.10769 (15)	0.0329 (4)
C1	0.3888 (4)	0.82269 (17)	0.30991 (14)	0.0161 (3)
C2	0.3511 (4)	0.67337 (17)	0.34707 (14)	0.0164 (3)
H2A	0.223831	0.622462	0.425784	0.020*
C3	0.4970 (4)	0.59800 (17)	0.27054 (14)	0.0169 (3)
C4	0.6811 (4)	0.67547 (18)	0.15490 (15)	0.0186 (4)
H4	0.783049	0.625313	0.101590	0.022*
C5	0.7172 (4)	0.82338 (18)	0.11701 (15)	0.0194 (4)
H5	0.841506	0.874346	0.037700	0.023*
C6	0.5730 (4)	0.89857 (18)	0.19389 (15)	0.0184 (4)
H6	0.599376	1.000494	0.167874	0.022*
C7	0.2220 (4)	0.89969 (17)	0.39315 (14)	0.0163 (3)
C8	0.4606 (4)	0.43609 (17)	0.31271 (15)	0.0199 (4)
H8A	0.694016	0.380445	0.335739	0.024*
H8B	0.289201	0.404683	0.388834	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0233 (6)	0.0168 (6)	0.0193 (6)	−0.0012 (4)	0.0030 (5)	−0.0088 (5)
O2	0.0299 (6)	0.0149 (6)	0.0238 (6)	−0.0030 (5)	0.0068 (5)	−0.0104 (5)
N1	0.0233 (7)	0.0237 (8)	0.0357 (8)	0.0019 (6)	−0.0050 (6)	−0.0198 (7)
N2	0.0256 (7)	0.0207 (7)	0.0214 (7)	−0.0072 (6)	−0.0005 (6)	−0.0084 (6)
N3	0.0339 (9)	0.0411 (10)	0.0325 (8)	−0.0096 (7)	0.0085 (7)	−0.0250 (8)
C1	0.0137 (7)	0.0182 (8)	0.0184 (8)	0.0015 (6)	−0.0040 (6)	−0.0092 (6)
C2	0.0122 (7)	0.0207 (8)	0.0169 (8)	0.0006 (6)	−0.0011 (6)	−0.0085 (6)
C3	0.0123 (7)	0.0190 (8)	0.0221 (8)	0.0019 (6)	−0.0048 (6)	−0.0107 (6)
C4	0.0144 (7)	0.0246 (9)	0.0204 (8)	0.0013 (6)	−0.0012 (6)	−0.0136 (7)
C5	0.0169 (7)	0.0233 (9)	0.0179 (8)	−0.0010 (6)	0.0012 (6)	−0.0089 (7)
C6	0.0170 (7)	0.0182 (8)	0.0204 (8)	0.0002 (6)	−0.0028 (6)	−0.0081 (7)
C7	0.0149 (7)	0.0168 (8)	0.0178 (8)	0.0011 (6)	−0.0031 (6)	−0.0074 (6)
C8	0.0187 (8)	0.0209 (9)	0.0220 (8)	−0.0020 (6)	0.0011 (6)	−0.0111 (7)

Geometric parameters (Å, º)

O1—C7	1.2337 (18)	C2—C3	1.388 (2)
O2—H2	0.90 (3)	C3—C4	1.397 (2)
O2—C7	1.3151 (19)	C3—C8	1.504 (2)
N1—N2	1.2364 (19)	C4—H4	0.9500
N1—C8	1.485 (2)	C4—C5	1.377 (2)
N2—N3	1.1337 (19)	C5—H5	0.9500
C1—C2	1.392 (2)	C5—C6	1.388 (2)
C1—C6	1.397 (2)	C6—H6	0.9500
C1—C7	1.482 (2)	C8—H8A	0.9900
C2—H2A	0.9500	C8—H8B	0.9900
C7—O2—H2	110.5 (15)	C4—C5—H5	119.8
N2—N1—C8	115.34 (13)	C4—C5—C6	120.46 (14)
N3—N2—N1	173.10 (16)	C6—C5—H5	119.8
C2—C1—C6	119.94 (14)	C1—C6—H6	120.4
C2—C1—C7	119.07 (13)	C5—C6—C1	119.25 (15)
C6—C1—C7	120.97 (13)	C5—C6—H6	120.4
C1—C2—H2A	119.6	O1—C7—O2	122.90 (14)
C3—C2—C1	120.81 (14)	O1—C7—C1	122.22 (13)
C3—C2—H2A	119.6	O2—C7—C1	114.88 (13)
C2—C3—C4	118.53 (14)	N1—C8—C3	111.77 (13)
C2—C3—C8	120.37 (14)	N1—C8—H8A	109.3
C4—C3—C8	121.10 (14)	N1—C8—H8B	109.3
C3—C4—H4	119.5	C3—C8—H8A	109.3
C5—C4—C3	121.01 (14)	C3—C8—H8B	109.3
C5—C4—H4	119.5	H8A—C8—H8B	107.9
N2—N1—C8—C3	108.18 (15)	C4—C3—C8—N1	−49.36 (18)
C1—C2—C3—C4	−0.4 (2)	C4—C5—C6—C1	−0.4 (2)
C1—C2—C3—C8	178.84 (13)	C6—C1—C2—C3	0.5 (2)
C2—C1—C6—C5	−0.1 (2)	C6—C1—C7—O1	173.70 (14)
C2—C1—C7—O1	−4.4 (2)	C6—C1—C7—O2	−6.1 (2)
C2—C1—C7—O2	175.81 (13)	C7—C1—C2—C3	178.66 (13)
C2—C3—C4—C5	−0.2 (2)	C7—C1—C6—C5	−178.22 (13)
C2—C3—C8—N1	131.44 (14)	C8—C3—C4—C5	−179.37 (14)
C3—C4—C5—C6	0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.90 (3)	1.73 (3)	2.6346 (15)	176 (2)

Symmetry code: (i) −x, −y+2, −z+1.