Polymorphic structures of 3-phenyl-1H-1,3-benzo­diazol-2(3H)-one

The two polymorphic structures of 3-phenyl-1H-1,3-benzo­diazol-2(3H)-one (I and II) exhibit identical bond distances and angles except for the C—N—C—C torsion angle between the benzimidazolone backbone and the phenyl substituent, which has an effect on the crystal packing and supra­molecular features. The structure of I contains a stronger C=O...H—N hydrogen-bonding inter­action and a weaker π–π inter­action between adjacent bezimidazolone moieties in comparison to II.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.104
• Data-to-parameter ratio = 16.2

Structure: II

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.099
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........          . Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.0 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009).

3-Phenyl-1H-1,3-benzodiazol-2(3H)-one (I)

Crystal data

C13H10N2O	F(000) = 880
Mr = 210.23	Dx = 1.377 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.0187 (9) Å	Cell parameters from 2753 reflections
b = 6.4455 (3) Å	θ = 2.3–27.5°
c = 18.7315 (10) Å	µ = 0.09 mm^−1
β = 111.181 (3)°	T = 193 K
V = 2028.50 (18) Å^3	NEEDLE, colourless
Z = 8	0.51 × 0.23 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer	1956 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.031
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 27.6°, θmin = 2.3°
Tmin = 0.699, Tmax = 0.746	h = −23→23
9328 measured reflections	k = −8→8
2350 independent reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 1.4081P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2350 reflections	Δρmax = 0.18 e Å^−3
145 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.

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

	x	y	z	Uiso*/Ueq
O1	0.60223 (5)	0.96614 (15)	0.57745 (5)	0.0239 (2)
N3	0.53005 (6)	0.77512 (18)	0.46886 (6)	0.0210 (3)
H3	0.488955	0.857863	0.448435	0.025*
N1	0.64477 (6)	0.64976 (18)	0.54578 (6)	0.0199 (3)
C8	0.71782 (7)	0.6314 (2)	0.60949 (7)	0.0200 (3)
C7A	0.61292 (7)	0.5048 (2)	0.48703 (7)	0.0198 (3)
C3A	0.54019 (7)	0.5865 (2)	0.43844 (7)	0.0202 (3)
C2	0.59267 (7)	0.8152 (2)	0.53505 (7)	0.0201 (3)
C9	0.73216 (8)	0.4585 (2)	0.65660 (7)	0.0242 (3)
H9	0.694564	0.348538	0.645522	0.029*
C13	0.77316 (7)	0.7904 (2)	0.62403 (7)	0.0230 (3)
H13	0.763240	0.907155	0.590917	0.028*
C7	0.64074 (8)	0.3170 (2)	0.47242 (8)	0.0236 (3)
H7	0.689738	0.261391	0.506014	0.028*
C4	0.49365 (8)	0.4809 (2)	0.37362 (7)	0.0238 (3)
H4	0.443989	0.534926	0.340804	0.029*
C5	0.52220 (8)	0.2924 (2)	0.35821 (8)	0.0274 (3)
H5	0.491700	0.217059	0.313667	0.033*
C10	0.80220 (8)	0.4481 (2)	0.72020 (8)	0.0275 (3)
H10	0.812386	0.330940	0.753147	0.033*
C6	0.59439 (8)	0.2116 (2)	0.40654 (8)	0.0266 (3)
H6	0.612378	0.082452	0.394429	0.032*
C12	0.84327 (8)	0.7775 (2)	0.68750 (8)	0.0274 (3)
H12	0.881670	0.885313	0.697783	0.033*
C11	0.85719 (8)	0.6075 (2)	0.73576 (7)	0.0283 (3)
H11	0.904654	0.600345	0.779703	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0232 (5)	0.0213 (5)	0.0244 (5)	0.0026 (4)	0.0052 (4)	−0.0008 (4)
N3	0.0185 (5)	0.0202 (6)	0.0217 (5)	0.0040 (4)	0.0041 (4)	0.0023 (4)
N1	0.0177 (5)	0.0193 (6)	0.0223 (5)	0.0027 (4)	0.0068 (4)	0.0014 (4)
C8	0.0177 (6)	0.0243 (8)	0.0193 (6)	0.0038 (5)	0.0083 (5)	0.0019 (5)
C7A	0.0191 (6)	0.0213 (7)	0.0216 (6)	−0.0015 (5)	0.0105 (5)	0.0018 (5)
C3A	0.0205 (6)	0.0207 (7)	0.0218 (6)	0.0006 (5)	0.0106 (5)	0.0032 (5)
C2	0.0195 (6)	0.0207 (7)	0.0209 (6)	0.0012 (5)	0.0081 (5)	0.0031 (5)
C9	0.0234 (6)	0.0248 (8)	0.0269 (7)	0.0031 (6)	0.0122 (5)	0.0037 (6)
C13	0.0221 (6)	0.0232 (8)	0.0244 (6)	0.0019 (5)	0.0095 (5)	0.0030 (5)
C7	0.0216 (6)	0.0236 (8)	0.0300 (7)	0.0022 (5)	0.0145 (5)	0.0029 (6)
C4	0.0229 (6)	0.0272 (8)	0.0210 (6)	−0.0022 (6)	0.0076 (5)	0.0025 (5)
C5	0.0333 (7)	0.0278 (9)	0.0251 (7)	−0.0077 (6)	0.0152 (6)	−0.0037 (6)
C10	0.0300 (7)	0.0295 (9)	0.0239 (6)	0.0100 (6)	0.0109 (5)	0.0071 (6)
C6	0.0322 (7)	0.0221 (8)	0.0327 (7)	−0.0013 (6)	0.0203 (6)	−0.0021 (6)
C12	0.0220 (6)	0.0306 (9)	0.0288 (7)	−0.0010 (6)	0.0083 (5)	−0.0044 (6)
C11	0.0232 (6)	0.0369 (9)	0.0211 (6)	0.0088 (6)	0.0037 (5)	−0.0022 (6)

Geometric parameters (Å, º)

O1—C2	1.2282 (16)	C13—H13	0.9500
N3—H3	0.8800	C13—C12	1.3896 (18)
N3—C3A	1.3824 (18)	C7—H7	0.9500
N3—C2	1.3660 (16)	C7—C6	1.3920 (19)
N1—C8	1.4266 (15)	C4—H4	0.9500
N1—C7A	1.3988 (17)	C4—C5	1.390 (2)
N1—C2	1.3864 (17)	C5—H5	0.9500
C8—C9	1.3868 (19)	C5—C6	1.390 (2)
C8—C13	1.3867 (19)	C10—H10	0.9500
C7A—C3A	1.4004 (17)	C10—C11	1.384 (2)
C7A—C7	1.375 (2)	C6—H6	0.9500
C3A—C4	1.3803 (18)	C12—H12	0.9500
C9—H9	0.9500	C12—C11	1.384 (2)
C9—C10	1.3893 (18)	C11—H11	0.9500
C3A—N3—H3	124.7	C12—C13—H13	120.3
C2—N3—H3	124.7	C7A—C7—H7	121.3
C2—N3—C3A	110.58 (11)	C7A—C7—C6	117.46 (12)
C7A—N1—C8	126.52 (11)	C6—C7—H7	121.3
C2—N1—C8	123.83 (11)	C3A—C4—H4	121.3
C2—N1—C7A	109.60 (10)	C3A—C4—C5	117.46 (12)
C9—C8—N1	120.15 (12)	C5—C4—H4	121.3
C13—C8—N1	118.93 (12)	C4—C5—H5	119.3
C13—C8—C9	120.91 (12)	C4—C5—C6	121.45 (13)
N1—C7A—C3A	106.37 (12)	C6—C5—H5	119.3
C7—C7A—N1	131.98 (12)	C9—C10—H10	119.9
C7—C7A—C3A	121.64 (12)	C11—C10—C9	120.28 (14)
N3—C3A—C7A	107.14 (11)	C11—C10—H10	119.9
C4—C3A—N3	131.89 (12)	C7—C6—H6	119.5
C4—C3A—C7A	120.97 (13)	C5—C6—C7	121.00 (14)
O1—C2—N3	127.84 (12)	C5—C6—H6	119.5
O1—C2—N1	125.88 (11)	C13—C12—H12	120.0
N3—C2—N1	106.28 (11)	C11—C12—C13	120.03 (13)
C8—C9—H9	120.4	C11—C12—H12	120.0
C8—C9—C10	119.16 (14)	C10—C11—C12	120.23 (12)
C10—C9—H9	120.4	C10—C11—H11	119.9
C8—C13—H13	120.3	C12—C11—H11	119.9
C8—C13—C12	119.38 (13)
N3—C3A—C4—C5	178.80 (13)	C3A—N3—C2—O1	−178.55 (13)
N1—C8—C9—C10	−177.25 (12)	C3A—N3—C2—N1	1.45 (14)
N1—C8—C13—C12	177.74 (12)	C3A—C7A—C7—C6	0.98 (19)
N1—C7A—C3A—N3	−0.29 (13)	C3A—C4—C5—C6	0.7 (2)
N1—C7A—C3A—C4	179.34 (11)	C2—N3—C3A—C7A	−0.73 (14)
N1—C7A—C7—C6	−178.35 (12)	C2—N3—C3A—C4	179.69 (13)
C8—N1—C7A—C3A	178.81 (11)	C2—N1—C8—C9	123.03 (14)
C8—N1—C7A—C7	−1.8 (2)	C2—N1—C8—C13	−55.86 (17)
C8—N1—C2—O1	0.7 (2)	C2—N1—C7A—C3A	1.19 (14)
C8—N1—C2—N3	−179.32 (11)	C2—N1—C7A—C7	−179.40 (13)
C8—C9—C10—C11	−0.6 (2)	C9—C8—C13—C12	−1.1 (2)
C8—C13—C12—C11	−0.3 (2)	C9—C10—C11—C12	−0.8 (2)
C7A—N1—C8—C9	−54.27 (17)	C13—C8—C9—C10	1.62 (19)
C7A—N1—C8—C13	126.85 (14)	C13—C12—C11—C10	1.3 (2)
C7A—N1—C2—O1	178.38 (12)	C7—C7A—C3A—N3	−179.77 (11)
C7A—N1—C2—N3	−1.62 (14)	C7—C7A—C3A—C4	−0.14 (19)
C7A—C3A—C4—C5	−0.72 (19)	C4—C5—C6—C7	0.1 (2)
C7A—C7—C6—C5	−0.96 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1^i	0.88	1.91	2.7786 (14)	177

Symmetry code: (i) −x+1, −y+2, −z+1.

(II)

Crystal data

C13H10N2O	Dx = 1.408 Mg m^−3
Mr = 210.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9912 reflections
a = 13.7925 (3) Å	θ = 2.5–28.3°
b = 7.2652 (1) Å	µ = 0.09 mm^−1
c = 19.7956 (4) Å	T = 193 K
V = 1983.62 (6) Å^3	BLOCK, colourless
Z = 8	0.37 × 0.33 × 0.19 mm
F(000) = 880

Data collection

Bruker APEXII CCD diffractometer	2203 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.036
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 28.4°, θmin = 2.1°
Tmin = 0.712, Tmax = 0.746	h = −18→18
34068 measured reflections	k = −8→9
2479 independent reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 1.3866P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2479 reflections	Δρmax = 0.25 e Å^−3
145 parameters	Δρmin = −0.37 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.

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

	x	y	z	Uiso*/Ueq
O1	0.45568 (7)	0.03382 (12)	0.59030 (4)	0.0202 (2)
N1	0.38806 (7)	0.32974 (13)	0.58960 (5)	0.0156 (2)
N3	0.43199 (7)	0.20514 (13)	0.49242 (5)	0.0162 (2)
H3	0.452728	0.125653	0.462151	0.019*
C7A	0.37019 (8)	0.46038 (16)	0.53914 (6)	0.0150 (2)
C2	0.42885 (8)	0.17358 (16)	0.56054 (6)	0.0162 (2)
C8	0.37484 (8)	0.35772 (16)	0.66031 (6)	0.0164 (2)
C3A	0.39783 (8)	0.38031 (16)	0.47791 (6)	0.0152 (2)
C7	0.33606 (8)	0.63906 (16)	0.54215 (6)	0.0176 (2)
H7	0.319418	0.694844	0.583974	0.021*
C4	0.38813 (8)	0.47304 (17)	0.41748 (6)	0.0178 (2)
H4	0.405896	0.417587	0.375818	0.021*
C5	0.35117 (8)	0.65146 (17)	0.42007 (6)	0.0195 (2)
H5	0.342230	0.718091	0.379252	0.023*
C9	0.44915 (9)	0.31474 (17)	0.70512 (6)	0.0198 (2)
H9	0.507674	0.261337	0.689104	0.024*
C13	0.28837 (9)	0.43311 (16)	0.68360 (6)	0.0203 (3)
H13	0.237403	0.460514	0.652926	0.024*
C6	0.32707 (8)	0.73401 (17)	0.48132 (6)	0.0192 (2)
H6	0.304090	0.857272	0.481620	0.023*
C12	0.27728 (10)	0.46798 (17)	0.75227 (7)	0.0257 (3)
H12	0.218579	0.520089	0.768528	0.031*
C11	0.35128 (11)	0.42719 (17)	0.79701 (6)	0.0268 (3)
H11	0.343401	0.451607	0.843835	0.032*
C10	0.43697 (10)	0.35064 (18)	0.77346 (6)	0.0245 (3)
H10	0.487637	0.322592	0.804296	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0276 (5)	0.0164 (4)	0.0168 (4)	0.0051 (3)	0.0006 (3)	−0.0002 (3)
N1	0.0173 (4)	0.0150 (4)	0.0145 (4)	0.0021 (4)	0.0005 (3)	−0.0022 (4)
N3	0.0188 (5)	0.0157 (5)	0.0142 (4)	0.0028 (4)	0.0004 (4)	−0.0022 (4)
C7A	0.0122 (5)	0.0172 (5)	0.0156 (5)	−0.0013 (4)	−0.0007 (4)	−0.0008 (4)
C2	0.0157 (5)	0.0168 (5)	0.0161 (5)	0.0004 (4)	0.0004 (4)	−0.0027 (4)
C8	0.0215 (5)	0.0137 (5)	0.0140 (5)	−0.0014 (4)	0.0023 (4)	−0.0020 (4)
C3A	0.0119 (5)	0.0160 (5)	0.0178 (5)	0.0001 (4)	−0.0001 (4)	−0.0025 (4)
C7	0.0148 (5)	0.0177 (5)	0.0203 (5)	0.0006 (4)	0.0012 (4)	−0.0035 (4)
C4	0.0166 (5)	0.0208 (6)	0.0161 (5)	0.0002 (4)	0.0004 (4)	−0.0011 (4)
C5	0.0167 (5)	0.0215 (6)	0.0202 (6)	−0.0001 (5)	−0.0006 (4)	0.0039 (5)
C9	0.0219 (6)	0.0199 (5)	0.0176 (5)	−0.0022 (5)	0.0005 (4)	0.0000 (4)
C13	0.0241 (6)	0.0162 (5)	0.0205 (6)	0.0009 (5)	0.0031 (5)	−0.0014 (4)
C6	0.0151 (5)	0.0166 (5)	0.0258 (6)	0.0011 (4)	0.0004 (4)	0.0006 (5)
C12	0.0353 (7)	0.0180 (6)	0.0237 (6)	0.0025 (5)	0.0117 (5)	−0.0024 (5)
C11	0.0460 (8)	0.0188 (6)	0.0156 (5)	−0.0047 (6)	0.0058 (5)	−0.0031 (5)
C10	0.0340 (7)	0.0230 (6)	0.0166 (6)	−0.0066 (5)	−0.0028 (5)	0.0013 (5)

Geometric parameters (Å, º)

O1—C2	1.2309 (14)	C4—H4	0.9500
N1—C7A	1.3997 (15)	C4—C5	1.3939 (17)
N1—C2	1.3908 (14)	C5—H5	0.9500
N1—C8	1.4262 (14)	C5—C6	1.3928 (17)
N3—H3	0.8800	C9—H9	0.9500
N3—C2	1.3685 (15)	C9—C10	1.3880 (17)
N3—C3A	1.3872 (15)	C13—H13	0.9500
C7A—C3A	1.3976 (15)	C13—C12	1.3912 (17)
C7A—C7	1.3821 (16)	C6—H6	0.9500
C8—C9	1.3910 (17)	C12—H12	0.9500
C8—C13	1.3911 (16)	C12—C11	1.383 (2)
C3A—C4	1.3793 (16)	C11—H11	0.9500
C7—H7	0.9500	C11—C10	1.387 (2)
C7—C6	1.3933 (17)	C10—H10	0.9500
C7A—N1—C8	125.54 (10)	C5—C4—H4	121.4
C2—N1—C7A	109.23 (9)	C4—C5—H5	119.3
C2—N1—C8	125.02 (10)	C6—C5—C4	121.32 (11)
C2—N3—H3	124.8	C6—C5—H5	119.3
C2—N3—C3A	110.31 (9)	C8—C9—H9	120.3
C3A—N3—H3	124.8	C10—C9—C8	119.35 (12)
C3A—C7A—N1	106.78 (10)	C10—C9—H9	120.3
C7—C7A—N1	131.77 (11)	C8—C13—H13	120.3
C7—C7A—C3A	121.41 (11)	C8—C13—C12	119.33 (12)
O1—C2—N1	126.63 (11)	C12—C13—H13	120.3
O1—C2—N3	126.89 (11)	C7—C6—H6	119.4
N3—C2—N1	106.48 (10)	C5—C6—C7	121.19 (11)
C9—C8—N1	119.98 (10)	C5—C6—H6	119.4
C9—C8—C13	120.59 (11)	C13—C12—H12	119.8
C13—C8—N1	119.41 (10)	C11—C12—C13	120.36 (12)
N3—C3A—C7A	107.15 (10)	C11—C12—H12	119.8
C4—C3A—N3	131.35 (11)	C12—C11—H11	120.0
C4—C3A—C7A	121.50 (11)	C12—C11—C10	119.96 (12)
C7A—C7—H7	121.4	C10—C11—H11	120.0
C7A—C7—C6	117.27 (11)	C9—C10—H10	119.8
C6—C7—H7	121.4	C11—C10—C9	120.41 (12)
C3A—C4—H4	121.4	C11—C10—H10	119.8
C3A—C4—C5	117.24 (11)
N1—C7A—C3A—N3	−0.32 (12)	C8—N1—C7A—C3A	176.62 (10)
N1—C7A—C3A—C4	179.08 (10)	C8—N1—C7A—C7	−1.01 (19)
N1—C7A—C7—C6	179.56 (11)	C8—N1—C2—O1	3.36 (19)
N1—C8—C9—C10	177.03 (11)	C8—N1—C2—N3	−177.43 (10)
N1—C8—C13—C12	−177.13 (11)	C8—C9—C10—C11	0.53 (19)
N3—C3A—C4—C5	−179.65 (11)	C8—C13—C12—C11	−0.35 (19)
C7A—N1—C2—O1	178.21 (11)	C3A—N3—C2—O1	−178.39 (11)
C7A—N1—C2—N3	−2.59 (12)	C3A—N3—C2—N1	2.40 (12)
C7A—N1—C8—C9	−129.31 (12)	C3A—C7A—C7—C6	2.22 (16)
C7A—N1—C8—C13	48.81 (16)	C3A—C4—C5—C6	1.38 (17)
C7A—C3A—C4—C5	1.11 (17)	C7—C7A—C3A—N3	177.61 (10)
C7A—C7—C6—C5	0.27 (17)	C7—C7A—C3A—C4	−2.99 (17)
C2—N1—C7A—C3A	1.81 (12)	C4—C5—C6—C7	−2.11 (18)
C2—N1—C7A—C7	−175.82 (12)	C9—C8—C13—C12	0.98 (18)
C2—N1—C8—C9	44.70 (17)	C13—C8—C9—C10	−1.07 (18)
C2—N1—C8—C13	−137.18 (12)	C13—C12—C11—C10	−0.2 (2)
C2—N3—C3A—C7A	−1.31 (13)	C12—C11—C10—C9	0.1 (2)
C2—N3—C3A—C4	179.37 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1^i	0.88	2.00	2.8453 (13)	174

Symmetry code: (i) −x+1, −y, −z+1.