A first-order phase transition in Blatter's radical at high pressure

The crystal structure of Blatter's radical (1,3-di­phenyl-1,4-di­hydro­benzo[e][1,2,4]triazin-4-yl) has been investigated between ambient pressure and 6.07 GPa. The sample remains in a compressed form of the ambient-pressure phase up to 5.34 GPa, the largest direction of strain being parallel to the direction of π-stacking interactions. The bulk modulus is 7.4 (6) GPa, with a pressure derivative equal to 9.33 (11). As pressure increases, the phenyl groups attached to the N1 and C3 positions of the triazinyl moieties of neighbouring pairs of molecules approach each other, causing the former to begin to rotate between 3.42 to 5.34 GPa. The onset of this phenyl rotation may be interpreted as a second-order phase transition which introduces a new mode for accommodating pressure. It is premonitory to a first-order isosymmetric phase transition which occurs on increasing pressure from 5.34 to 5.54 GPa. Although the phase transition is driven by volume minimization, rather than relief of unfavourable contacts, it is accompanied by a sharp jump in the orientation of the rotation angle of the phenyl group. DFT calculations suggest that the adoption of a more planar conformation by the triazinyl moiety at the phase transition can be attributed to relief of intramolecular H...H contacts at the transition. Although no dimerization of the radicals occurs, the π-stacking interactions are compressed by 0.341 (3) Å between ambient pressure and 6.07 GPa.

Computing details

Cell refinement: SAINT V8.40A (Bruker, 2019) for mo_sp20030_0m_0p0000GPa, mo_sp20038_0m_0p3568GPa, mo_sp20040_0m_0p6591GPa, mo_sp20034_0m_0p8792GPa, mo_sp20041_0m_1p0994GPa, mo_sp20049_0m_2p1201GPa, mo_sp20037_0m_2p5349GPa, mo_sp20051_0m_2p5349GPa, mo_sp20039_0m_3p4218GPa, mo_sp20044_0m_4p7574GPa, mo_sp20048_0m_5p3456GPa, mo_sp20050_0m_5p5393GPa, mo_sp20052_0m_5p7631GPa, mo_sp20053_0m_6p0711GPa; SAINT V8.38A (Bruker, 2018) for sp20043_0m_1p3749GPa, sp20035_0m_1p8162GPa, sp20042_0m_4p0054GPa. Data reduction: SAINT V8.40A (Bruker, 2019) for mo_sp20030_0m_0p0000GPa, mo_sp20038_0m_0p3568GPa, mo_sp20040_0m_0p6591GPa, mo_sp20034_0m_0p8792GPa, mo_sp20041_0m_1p0994GPa, mo_sp20049_0m_2p1201GPa, mo_sp20037_0m_2p5349GPa, mo_sp20051_0m_2p5349GPa, mo_sp20039_0m_3p4218GPa, mo_sp20044_0m_4p7574GPa, mo_sp20048_0m_5p3456GPa, mo_sp20050_0m_5p5393GPa, mo_sp20052_0m_5p7631GPa, mo_sp20053_0m_6p0711GPa; SAINT V8.38A (Bruker, 2018) for sp20043_0m_1p3749GPa, sp20035_0m_1p8162GPa, sp20042_0m_4p0054GPa. For all structures, program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014); program(s) used to refine structure: XL (Sheldrick, 2008); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009).

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20030_0m_0p0000GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.319 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.4887 (4) Å	Cell parameters from 1691 reflections
b = 6.9632 (2) Å	θ = 3.1–26.9°
c = 19.8755 (7) Å	µ = 0.08 mm^−1
β = 99.441 (2)°	T = 298 K
V = 1431.94 (9) Å^3	Block, clear dark brown
Z = 4	0.6 × 0.4 × 0.2 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	2511 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	1422 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.044
Detector resolution: 7.9 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1139 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.8684. The λ/2 correction factor is Not present.	k = −7→8
Tmin = 0.648, Tmax = 0.746	l = −23→23
8006 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.057	w = 1/[σ^2(Fo^2) + (0.0809P)^2 + 0.4711P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.188	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.20 e Å^−3
2511 reflections	Δρmin = −0.17 e Å^−3
200 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.047 (9)
Primary atom site location: dual

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. PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 3 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 2 Note PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ·········.. 3.2 Low PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by 3 Check

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.47277 (18)	0.7135 (3)	0.65732 (10)	0.0500 (6)
N2	0.44116 (18)	0.7102 (3)	0.72165 (10)	0.0493 (6)
N3	0.21677 (19)	0.7023 (3)	0.67222 (10)	0.0496 (6)
C1	0.3146 (2)	0.7057 (3)	0.72431 (12)	0.0445 (6)
C2	0.2504 (2)	0.6947 (4)	0.60833 (12)	0.0476 (6)
C7	0.1546 (2)	0.6784 (4)	0.55078 (13)	0.0572 (7)
H7	0.068123	0.678123	0.556031	0.069*
C6	0.1861 (3)	0.6627 (4)	0.48665 (14)	0.0623 (8)
H6	0.121366	0.650566	0.448864	0.075*
C5	0.3151 (3)	0.6651 (4)	0.47839 (14)	0.0626 (8)
H5	0.336156	0.654068	0.434883	0.075*
C4	0.4120 (3)	0.6835 (4)	0.53350 (13)	0.0572 (7)
H4	0.497965	0.685476	0.527336	0.069*
C3	0.3806 (2)	0.6993 (3)	0.59884 (12)	0.0462 (6)
C14	0.6092 (2)	0.7135 (4)	0.65722 (12)	0.0510 (7)
C19	0.6638 (3)	0.8499 (4)	0.62063 (14)	0.0623 (8)
H19	0.612392	0.943344	0.596110	0.075*
C18	0.7956 (3)	0.8469 (5)	0.62065 (15)	0.0754 (10)
H18	0.832406	0.937338	0.595260	0.091*
C17	0.8721 (3)	0.7130 (6)	0.65738 (15)	0.0811 (11)
H17	0.960693	0.712723	0.657157	0.097*
C16	0.8179 (3)	0.5772 (6)	0.69507 (15)	0.0787 (10)
H16	0.869993	0.485402	0.720083	0.094*
C15	0.6851 (2)	0.5784 (5)	0.69543 (13)	0.0639 (8)
H15	0.648197	0.488986	0.721193	0.077*
C8	0.2822 (2)	0.7030 (3)	0.79431 (12)	0.0458 (6)
C9	0.1550 (2)	0.7185 (4)	0.80359 (14)	0.0551 (7)
H9	0.089992	0.731916	0.766000	0.066*
C10	0.1239 (3)	0.7141 (4)	0.86849 (15)	0.0642 (8)
H10	0.038003	0.726430	0.874163	0.077*
C11	0.2180 (3)	0.6917 (4)	0.92472 (15)	0.0648 (8)
H11	0.196324	0.687290	0.968234	0.078*
C12	0.3449 (3)	0.6760 (4)	0.91559 (14)	0.0659 (8)
H12	0.409440	0.661195	0.953332	0.079*
C13	0.3776 (3)	0.6821 (4)	0.85094 (13)	0.0577 (7)
H13	0.463724	0.672127	0.845482	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0398 (11)	0.0673 (14)	0.0437 (12)	0.0008 (10)	0.0098 (9)	0.0009 (10)
N2	0.0432 (11)	0.0626 (13)	0.0432 (12)	−0.0003 (10)	0.0104 (9)	−0.0016 (10)
N3	0.0433 (11)	0.0584 (13)	0.0473 (12)	0.0024 (10)	0.0080 (9)	−0.0011 (10)
C1	0.0399 (12)	0.0456 (13)	0.0481 (14)	0.0015 (10)	0.0080 (11)	−0.0007 (11)
C2	0.0457 (13)	0.0522 (14)	0.0453 (14)	0.0047 (11)	0.0086 (11)	0.0009 (11)
C7	0.0466 (14)	0.0721 (18)	0.0514 (15)	0.0042 (13)	0.0031 (12)	−0.0021 (13)
C6	0.0566 (16)	0.079 (2)	0.0480 (16)	0.0061 (14)	−0.0011 (12)	−0.0028 (13)
C5	0.0613 (16)	0.078 (2)	0.0483 (16)	0.0048 (15)	0.0099 (13)	−0.0028 (14)
C4	0.0503 (14)	0.0748 (18)	0.0473 (15)	0.0026 (13)	0.0104 (12)	−0.0008 (13)
C3	0.0450 (13)	0.0512 (14)	0.0425 (14)	0.0021 (11)	0.0075 (10)	−0.0013 (11)
C14	0.0390 (12)	0.0697 (17)	0.0449 (14)	0.0000 (12)	0.0090 (10)	−0.0060 (12)
C19	0.0530 (15)	0.0792 (19)	0.0558 (16)	−0.0048 (14)	0.0121 (12)	0.0003 (14)
C18	0.0526 (16)	0.117 (3)	0.0582 (18)	−0.0184 (18)	0.0144 (14)	−0.0036 (18)
C17	0.0454 (15)	0.149 (3)	0.0494 (17)	−0.0028 (19)	0.0103 (13)	−0.0115 (19)
C16	0.0510 (15)	0.128 (3)	0.0547 (17)	0.0218 (19)	0.0023 (13)	0.0022 (19)
C15	0.0507 (14)	0.092 (2)	0.0499 (16)	0.0073 (15)	0.0105 (12)	0.0085 (15)
C8	0.0452 (13)	0.0479 (13)	0.0454 (14)	−0.0038 (11)	0.0110 (11)	−0.0030 (11)
C9	0.0488 (14)	0.0648 (16)	0.0531 (16)	−0.0035 (13)	0.0130 (12)	−0.0030 (13)
C10	0.0584 (16)	0.0738 (19)	0.0659 (19)	−0.0050 (14)	0.0267 (14)	−0.0074 (15)
C11	0.0762 (19)	0.0720 (19)	0.0502 (16)	−0.0083 (16)	0.0221 (14)	−0.0049 (14)
C12	0.0635 (17)	0.085 (2)	0.0487 (16)	−0.0058 (16)	0.0067 (13)	−0.0007 (14)
C13	0.0503 (14)	0.0743 (18)	0.0492 (15)	−0.0007 (13)	0.0097 (12)	−0.0018 (13)

Geometric parameters (Å, º)

N1—N2	1.373 (3)	C19—C18	1.383 (4)
N1—C3	1.388 (3)	C18—H18	0.9300
N1—C14	1.432 (3)	C18—C17	1.362 (5)
N2—C1	1.338 (3)	C17—H17	0.9300
N3—C1	1.333 (3)	C17—C16	1.385 (5)
N3—C2	1.374 (3)	C16—H16	0.9300
C1—C8	1.486 (3)	C16—C15	1.394 (4)
C2—C7	1.398 (3)	C15—H15	0.9300
C2—C3	1.409 (3)	C8—C9	1.380 (3)
C7—H7	0.9300	C8—C13	1.386 (3)
C7—C6	1.373 (4)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.382 (4)
C6—C5	1.390 (4)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.373 (4)
C5—C4	1.372 (4)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.377 (4)
C4—C3	1.395 (3)	C12—H12	0.9300
C14—C19	1.377 (4)	C12—C13	1.384 (4)
C14—C15	1.377 (4)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	122.51 (18)	C18—C19—H19	120.3
N2—N1—C14	113.30 (18)	C19—C18—H18	119.6
C3—N1—C14	123.91 (19)	C17—C18—C19	120.8 (3)
C1—N2—N1	115.48 (19)	C17—C18—H18	119.6
C1—N3—C2	115.9 (2)	C18—C17—H17	120.0
N2—C1—C8	114.7 (2)	C18—C17—C16	120.0 (3)
N3—C1—N2	127.8 (2)	C16—C17—H17	120.0
N3—C1—C8	117.5 (2)	C17—C16—H16	120.1
N3—C2—C7	120.0 (2)	C17—C16—C15	119.8 (3)
N3—C2—C3	121.6 (2)	C15—C16—H16	120.1
C7—C2—C3	118.3 (2)	C14—C15—C16	119.3 (3)
C2—C7—H7	119.5	C14—C15—H15	120.4
C6—C7—C2	121.1 (2)	C16—C15—H15	120.4
C6—C7—H7	119.5	C9—C8—C1	119.9 (2)
C7—C6—H6	120.1	C9—C8—C13	119.0 (2)
C7—C6—C5	119.7 (2)	C13—C8—C1	121.1 (2)
C5—C6—H6	120.1	C8—C9—H9	119.9
C6—C5—H5	119.5	C8—C9—C10	120.3 (3)
C4—C5—C6	121.0 (3)	C10—C9—H9	119.9
C4—C5—H5	119.5	C9—C10—H10	119.5
C5—C4—H4	120.2	C11—C10—C9	120.9 (3)
C5—C4—C3	119.6 (2)	C11—C10—H10	119.5
C3—C4—H4	120.2	C10—C11—H11	120.6
N1—C3—C2	116.5 (2)	C10—C11—C12	118.9 (3)
N1—C3—C4	123.2 (2)	C12—C11—H11	120.6
C4—C3—C2	120.3 (2)	C11—C12—H12	119.6
C19—C14—N1	120.2 (2)	C11—C12—C13	120.8 (3)
C19—C14—C15	120.7 (2)	C13—C12—H12	119.6
C15—C14—N1	119.1 (2)	C8—C13—H13	120.0
C14—C19—H19	120.3	C12—C13—C8	120.1 (2)
C14—C19—C18	119.4 (3)	C12—C13—H13	120.0
N1—N2—C1—N3	0.7 (4)	C7—C6—C5—C4	−0.2 (4)
N1—N2—C1—C8	−179.78 (19)	C6—C5—C4—C3	0.3 (4)
N1—C14—C19—C18	−179.5 (3)	C5—C4—C3—N1	178.3 (2)
N1—C14—C15—C16	179.6 (3)	C5—C4—C3—C2	0.6 (4)
N2—N1—C3—C2	4.3 (3)	C3—N1—N2—C1	−4.4 (3)
N2—N1—C3—C4	−173.5 (2)	C3—N1—C14—C19	57.9 (3)
N2—N1—C14—C19	−128.1 (2)	C3—N1—C14—C15	−123.7 (3)
N2—N1—C14—C15	50.4 (3)	C3—C2—C7—C6	1.5 (4)
N2—C1—C8—C9	173.3 (2)	C14—N1—N2—C1	−178.6 (2)
N2—C1—C8—C13	−7.7 (3)	C14—N1—C3—C2	177.8 (2)
N3—C1—C8—C9	−7.1 (3)	C14—N1—C3—C4	0.0 (4)
N3—C1—C8—C13	171.9 (2)	C14—C19—C18—C17	−1.2 (5)
N3—C2—C7—C6	−177.4 (2)	C19—C14—C15—C16	−2.0 (4)
N3—C2—C3—N1	−0.5 (3)	C19—C18—C17—C16	0.3 (5)
N3—C2—C3—C4	177.4 (2)	C18—C17—C16—C15	−0.2 (5)
C1—N3—C2—C7	176.0 (2)	C17—C16—C15—C14	1.0 (5)
C1—N3—C2—C3	−2.8 (3)	C15—C14—C19—C18	2.1 (4)
C1—C8—C9—C10	179.3 (2)	C8—C9—C10—C11	−0.9 (4)
C1—C8—C13—C12	−178.7 (2)	C9—C8—C13—C12	0.3 (4)
C2—N3—C1—N2	2.9 (4)	C9—C10—C11—C12	0.8 (4)
C2—N3—C1—C8	−176.7 (2)	C10—C11—C12—C13	−0.2 (5)
C2—C7—C6—C5	−0.7 (4)	C11—C12—C13—C8	−0.4 (4)
C7—C2—C3—N1	−179.3 (2)	C13—C8—C9—C10	0.3 (4)
C7—C2—C3—C4	−1.4 (4)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20038_0m_0p3568GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.371 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.4160 (6) Å	Cell parameters from 2275 reflections
b = 6.8137 (4) Å	θ = 3.2–26.2°
c = 19.690 (2) Å	µ = 0.08 mm^−1
β = 99.691 (6)°	T = 295 K
V = 1377.5 (2) Å^3	Block, clear dark brown
Z = 4	0.18 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	968 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	641 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.041
Detector resolution: 7.9 pixels mm^-1	θmax = 26.4°, θmin = 2.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0501 before and 0.0399 after correction. The Ratio of minimum to maximum transmission is 0.9005. The λ/2 correction factor is Not present.	k = −8→8
Tmin = 0.671, Tmax = 0.745	l = −8→8
8076 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.2479P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
968 reflections	Δρmax = 0.09 e Å^−3
199 parameters	Δρmin = −0.08 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 0.3568 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ··· -2 Units PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 65 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4732 (2)	0.7121 (3)	0.6583 (3)	0.037 (3)
N2	0.4421 (2)	0.7081 (3)	0.7223 (3)	0.037 (3)
N3	0.2164 (2)	0.6985 (3)	0.6727 (4)	0.036 (3)
C1	0.3138 (3)	0.7026 (4)	0.7254 (4)	0.030 (3)
C2	0.2486 (3)	0.6921 (4)	0.6081 (4)	0.033 (3)
C7	0.1531 (3)	0.6745 (4)	0.5508 (4)	0.037 (3)
H7	0.066117	0.672148	0.556177	0.045*
C6	0.1836 (3)	0.6606 (5)	0.4864 (4)	0.044 (3)
H6	0.117324	0.648061	0.448622	0.052*
C5	0.3139 (3)	0.6649 (3)	0.4765 (3)	0.045 (3)
H5	0.334213	0.654947	0.432349	0.053*
C4	0.4111 (3)	0.6838 (4)	0.5326 (4)	0.040 (3)
H4	0.497724	0.687165	0.526484	0.048*
C3	0.3809 (3)	0.6980 (4)	0.5983 (4)	0.034 (3)
C14	0.61121 (19)	0.7125 (3)	0.6573 (3)	0.029 (3)
C19	0.6654 (2)	0.8514 (4)	0.6207 (3)	0.041 (4)
H19	0.613012	0.946484	0.595963	0.049*
C18	0.7981 (2)	0.8503 (4)	0.6204 (3)	0.054 (4)
H18	0.834896	0.943081	0.594858	0.065*
C17	0.8746 (3)	0.7130 (5)	0.6576 (4)	0.063 (4)
H17	0.963757	0.712357	0.657345	0.076*
C16	0.8212 (2)	0.5749 (5)	0.6958 (4)	0.054 (4)
H16	0.874270	0.482446	0.721530	0.065*
C15	0.6872 (2)	0.5745 (4)	0.6957 (3)	0.044 (4)
H15	0.650027	0.482046	0.721232	0.053*
C8	0.2831 (3)	0.6993 (4)	0.7961 (4)	0.033 (3)
C9	0.1536 (3)	0.7171 (4)	0.8052 (4)	0.039 (4)
H9	0.088039	0.732819	0.767282	0.047*
C10	0.1233 (3)	0.7112 (4)	0.8706 (4)	0.045 (4)
H10	0.036890	0.722658	0.876465	0.054*
C11	0.2178 (3)	0.6889 (4)	0.9268 (4)	0.047 (4)
H11	0.196291	0.685255	0.970754	0.057*
C12	0.3461 (3)	0.6718 (4)	0.9180 (4)	0.048 (3)
H12	0.411195	0.656274	0.956202	0.058*
C13	0.3782 (3)	0.6776 (4)	0.8533 (4)	0.041 (3)
H13	0.464933	0.666695	0.847986	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0278 (13)	0.0504 (13)	0.034 (9)	0.0009 (10)	0.007 (2)	−0.001 (2)
N2	0.0269 (13)	0.0509 (13)	0.035 (9)	−0.0010 (9)	0.005 (3)	−0.002 (2)
N3	0.0292 (14)	0.0460 (13)	0.031 (9)	0.0019 (10)	0.000 (3)	0.001 (2)
C1	0.0248 (14)	0.0342 (13)	0.031 (9)	−0.0001 (10)	0.002 (3)	0.000 (3)
C2	0.0333 (18)	0.0381 (14)	0.027 (9)	0.0023 (11)	0.004 (3)	−0.003 (3)
C7	0.0268 (15)	0.0554 (16)	0.027 (10)	0.0035 (12)	−0.003 (3)	0.002 (3)
C6	0.0432 (18)	0.0587 (17)	0.028 (11)	0.0032 (13)	0.004 (3)	−0.005 (4)
C5	0.0435 (15)	0.0617 (16)	0.029 (11)	0.0030 (12)	0.007 (3)	0.000 (3)
C4	0.0318 (16)	0.0574 (17)	0.032 (10)	0.0016 (12)	0.009 (3)	0.000 (3)
C3	0.0288 (16)	0.0394 (14)	0.033 (10)	0.0015 (11)	0.004 (3)	−0.002 (3)
C14	0.0238 (11)	0.0514 (14)	0.010 (10)	0.0010 (10)	0.001 (2)	−0.002 (2)
C19	0.0382 (13)	0.0577 (16)	0.027 (12)	−0.0039 (11)	0.006 (3)	−0.001 (2)
C18	0.0370 (14)	0.090 (2)	0.036 (14)	−0.0177 (13)	0.010 (3)	0.000 (3)
C17	0.0281 (13)	0.114 (3)	0.047 (13)	−0.0011 (15)	0.008 (3)	−0.002 (3)
C16	0.0386 (14)	0.100 (2)	0.020 (14)	0.0191 (14)	−0.005 (3)	0.003 (3)
C15	0.0375 (13)	0.0688 (18)	0.027 (12)	0.0053 (11)	0.009 (2)	0.005 (3)
C8	0.0322 (16)	0.0365 (13)	0.033 (9)	−0.0022 (11)	0.013 (3)	0.000 (3)
C9	0.0309 (16)	0.0496 (15)	0.036 (11)	−0.0010 (10)	0.006 (3)	0.002 (3)
C10	0.0387 (17)	0.0591 (17)	0.040 (12)	−0.0049 (13)	0.016 (3)	−0.002 (3)
C11	0.0562 (18)	0.0574 (17)	0.033 (12)	−0.0089 (13)	0.018 (3)	−0.003 (3)
C12	0.050 (2)	0.0609 (18)	0.034 (11)	−0.0040 (14)	0.007 (4)	0.001 (4)
C13	0.0315 (16)	0.0565 (16)	0.034 (10)	−0.0011 (13)	0.006 (3)	−0.003 (3)

Geometric parameters (Å, º)

N1—N2	1.352 (7)	C19—C18	1.383 (3)
N1—C3	1.397 (7)	C18—H18	0.9300
N1—C14	1.441 (3)	C18—C17	1.360 (5)
N2—C1	1.349 (4)	C17—H17	0.9300
N3—C1	1.323 (6)	C17—C16	1.378 (6)
N3—C2	1.371 (8)	C16—H16	0.9300
C1—C8	1.482 (7)	C16—C15	1.395 (3)
C2—C7	1.378 (7)	C15—H15	0.9300
C2—C3	1.423 (5)	C8—C9	1.395 (4)
C7—H7	0.9300	C8—C13	1.376 (7)
C7—C6	1.360 (8)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.377 (8)
C6—C5	1.405 (4)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.360 (7)
C5—C4	1.374 (7)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.381 (4)
C4—C3	1.385 (8)	C12—H12	0.9300
C14—C19	1.368 (5)	C12—C13	1.371 (8)
C14—C15	1.372 (5)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	123.3 (3)	C18—C19—H19	120.0
N2—N1—C14	114.2 (5)	C19—C18—H18	120.1
C3—N1—C14	122.3 (5)	C17—C18—C19	119.8 (4)
C1—N2—N1	115.9 (5)	C17—C18—H18	120.1
C1—N3—C2	116.9 (4)	C18—C17—H17	119.7
N2—C1—C8	114.5 (5)	C18—C17—C16	120.7 (3)
N3—C1—N2	126.9 (6)	C16—C17—H17	119.7
N3—C1—C8	118.5 (3)	C17—C16—H16	120.1
N3—C2—C7	120.5 (4)	C17—C16—C15	119.7 (3)
N3—C2—C3	121.3 (5)	C15—C16—H16	120.1
C7—C2—C3	118.2 (6)	C14—C15—C16	118.9 (3)
C2—C7—H7	119.4	C14—C15—H15	120.5
C6—C7—C2	121.3 (4)	C16—C15—H15	120.5
C6—C7—H7	119.4	C9—C8—C1	119.1 (5)
C7—C6—H6	119.6	C13—C8—C1	122.1 (3)
C7—C6—C5	120.8 (5)	C13—C8—C9	118.8 (6)
C5—C6—H6	119.6	C8—C9—H9	120.1
C6—C5—H5	120.4	C10—C9—C8	119.7 (5)
C4—C5—C6	119.2 (6)	C10—C9—H9	120.1
C4—C5—H5	120.4	C9—C10—H10	119.5
C5—C4—H4	119.8	C11—C10—C9	121.0 (4)
C5—C4—C3	120.3 (3)	C11—C10—H10	119.5
C3—C4—H4	119.8	C10—C11—H11	120.3
N1—C3—C2	115.5 (6)	C10—C11—C12	119.4 (6)
C4—C3—N1	124.3 (3)	C12—C11—H11	120.3
C4—C3—C2	120.2 (5)	C11—C12—H12	119.8
C19—C14—N1	120.7 (3)	C13—C12—C11	120.4 (6)
C19—C14—C15	120.9 (2)	C13—C12—H12	119.8
C15—C14—N1	118.4 (3)	C8—C13—H13	119.7
C14—C19—H19	120.0	C12—C13—C8	120.6 (4)
C14—C19—C18	120.0 (3)	C12—C13—H13	119.7
N1—N2—C1—N3	0.8 (4)	C7—C6—C5—C4	−0.2 (5)
N1—N2—C1—C8	−179.7 (2)	C6—C5—C4—C3	0.2 (5)
N1—C14—C19—C18	179.7 (5)	C5—C4—C3—N1	178.1 (2)
N1—C14—C15—C16	−179.2 (5)	C5—C4—C3—C2	0.3 (5)
N2—N1—C3—C2	4.1 (4)	C3—N1—N2—C1	−4.3 (4)
N2—N1—C3—C4	−173.8 (3)	C3—N1—C14—C19	58.0 (5)
N2—N1—C14—C19	−127.8 (4)	C3—N1—C14—C15	−124.1 (5)
N2—N1—C14—C15	50.1 (5)	C3—C2—C7—C6	0.8 (5)
N2—C1—C8—C9	172.4 (2)	C14—N1—N2—C1	−178.38 (19)
N2—C1—C8—C13	−8.1 (4)	C14—N1—C3—C2	177.7 (2)
N3—C1—C8—C9	−8.0 (4)	C14—N1—C3—C4	−0.2 (5)
N3—C1—C8—C13	171.4 (2)	C14—C19—C18—C17	−1.2 (7)
N3—C2—C7—C6	−177.5 (3)	C19—C14—C15—C16	−1.3 (7)
N3—C2—C3—N1	−0.5 (4)	C19—C18—C17—C16	−0.1 (8)
N3—C2—C3—C4	177.5 (3)	C18—C17—C16—C15	0.7 (8)
C1—N3—C2—C7	175.7 (2)	C17—C16—C15—C14	0.0 (7)
C1—N3—C2—C3	−2.6 (5)	C15—C14—C19—C18	1.9 (7)
C1—C8—C9—C10	179.0 (3)	C8—C9—C10—C11	0.2 (5)
C1—C8—C13—C12	−178.9 (3)	C9—C8—C13—C12	0.6 (5)
C2—N3—C1—N2	2.5 (4)	C9—C10—C11—C12	0.0 (5)
C2—N3—C1—C8	−176.9 (2)	C10—C11—C12—C13	0.1 (5)
C2—C7—C6—C5	−0.4 (6)	C11—C12—C13—C8	−0.4 (5)
C7—C2—C3—N1	−178.8 (2)	C13—C8—C9—C10	−0.5 (4)
C7—C2—C3—C4	−0.8 (4)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20040_0m_0p6591GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.396 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.3807 (7) Å	Cell parameters from 2218 reflections
b = 6.7430 (5) Å	θ = 3.2–24.6°
c = 19.605 (3) Å	µ = 0.09 mm^−1
β = 99.757 (8)°	T = 295 K
V = 1352.5 (2) Å^3	Block, clear dark brown
Z = 4	0.18 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	918 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	604 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.037
Detector resolution: 7.9 pixels mm^-1	θmax = 26.4°, θmin = 2.1°
φ and ω scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0633 before and 0.0418 after correction. The Ratio of minimum to maximum transmission is 0.9156. The λ/2 correction factor is Not present.	k = −8→8
Tmin = 0.683, Tmax = 0.745	l = −8→8
6476 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 0.1489P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
918 reflections	Δρmax = 0.07 e Å^−3
199 parameters	Δρmin = −0.11 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 0.6591 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 80 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4737 (2)	0.7112 (3)	0.6584 (3)	0.037 (3)
N2	0.4422 (2)	0.7061 (3)	0.7229 (3)	0.038 (3)
N3	0.2157 (2)	0.6958 (3)	0.6730 (3)	0.036 (3)
C1	0.3137 (2)	0.7002 (4)	0.7260 (4)	0.031 (3)
C2	0.2483 (3)	0.6906 (4)	0.6080 (4)	0.033 (3)
C7	0.1520 (3)	0.6729 (4)	0.5504 (4)	0.039 (3)
H7	0.064762	0.670168	0.555874	0.046*
C6	0.1826 (3)	0.6594 (5)	0.4857 (4)	0.043 (3)
H6	0.115919	0.646329	0.447786	0.051*
C5	0.3126 (2)	0.6649 (3)	0.4754 (3)	0.046 (3)
H5	0.332617	0.655638	0.431009	0.055*
C4	0.4102 (3)	0.6843 (4)	0.5317 (4)	0.040 (3)
H4	0.496902	0.688652	0.525396	0.048*
C3	0.3808 (3)	0.6973 (4)	0.5979 (4)	0.034 (3)
C14	0.61171 (19)	0.7114 (3)	0.6578 (3)	0.031 (3)
C19	0.6658 (2)	0.8517 (3)	0.6206 (3)	0.047 (4)
H19	0.613001	0.946961	0.595387	0.056*
C18	0.7989 (2)	0.8511 (4)	0.6207 (3)	0.052 (4)
H18	0.835994	0.945196	0.595243	0.063*
C17	0.8761 (2)	0.7115 (5)	0.6584 (3)	0.053 (4)
H17	0.965797	0.711476	0.658704	0.063*
C16	0.8220 (2)	0.5719 (5)	0.6957 (3)	0.056 (4)
H16	0.874989	0.476887	0.720971	0.067*
C15	0.68818 (19)	0.5718 (4)	0.6960 (3)	0.042 (3)
H15	0.651147	0.478406	0.721788	0.051*
C8	0.2828 (3)	0.6974 (3)	0.7971 (4)	0.031 (3)
C9	0.1529 (2)	0.7152 (4)	0.8062 (4)	0.042 (4)
H9	0.086930	0.730503	0.768095	0.050*
C10	0.1226 (3)	0.7100 (4)	0.8720 (4)	0.047 (4)
H10	0.035895	0.721982	0.877911	0.056*
C11	0.2180 (3)	0.6874 (3)	0.9287 (4)	0.052 (4)
H11	0.196370	0.683970	0.972798	0.062*
C12	0.3467 (3)	0.6699 (4)	0.9202 (4)	0.046 (3)
H12	0.412006	0.654425	0.958584	0.055*
C13	0.3783 (3)	0.6752 (4)	0.8550 (4)	0.040 (3)
H13	0.465318	0.663604	0.849718	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0231 (12)	0.0470 (13)	0.041 (9)	0.0008 (9)	0.007 (2)	0.002 (2)
N2	0.0253 (13)	0.0445 (13)	0.045 (9)	−0.0010 (9)	0.009 (2)	−0.001 (2)
N3	0.0264 (14)	0.0391 (13)	0.040 (9)	0.0015 (9)	0.001 (3)	0.002 (2)
C1	0.0252 (14)	0.0279 (13)	0.038 (9)	0.0002 (10)	0.002 (3)	−0.001 (3)
C2	0.0292 (17)	0.0331 (15)	0.037 (9)	0.0014 (10)	0.005 (3)	−0.002 (3)
C7	0.0253 (14)	0.0493 (17)	0.039 (10)	0.0030 (11)	−0.002 (3)	0.001 (3)
C6	0.0381 (16)	0.0513 (17)	0.037 (10)	0.0023 (12)	0.002 (3)	−0.007 (3)
C5	0.0375 (14)	0.0551 (16)	0.043 (10)	0.0026 (11)	0.003 (3)	0.004 (3)
C4	0.0317 (16)	0.0490 (17)	0.040 (10)	0.0023 (12)	0.009 (3)	0.003 (3)
C3	0.0277 (15)	0.0324 (14)	0.041 (9)	0.0014 (10)	0.004 (3)	−0.002 (3)
C14	0.0233 (11)	0.0436 (14)	0.025 (10)	0.0003 (10)	0.004 (2)	−0.005 (2)
C19	0.0334 (12)	0.0480 (17)	0.058 (12)	−0.0031 (10)	0.004 (3)	0.003 (2)
C18	0.0361 (14)	0.079 (2)	0.044 (13)	−0.0166 (12)	0.012 (3)	−0.001 (3)
C17	0.0260 (12)	0.104 (3)	0.027 (13)	−0.0001 (14)	0.003 (3)	−0.011 (3)
C16	0.0357 (13)	0.092 (2)	0.037 (13)	0.0166 (13)	−0.003 (3)	0.009 (3)
C15	0.0357 (12)	0.0572 (17)	0.035 (11)	0.0034 (10)	0.010 (2)	0.004 (2)
C8	0.0295 (15)	0.0287 (14)	0.037 (9)	−0.0019 (10)	0.008 (3)	−0.001 (3)
C9	0.0290 (15)	0.0419 (15)	0.055 (11)	−0.0023 (10)	0.006 (3)	0.001 (3)
C10	0.0364 (16)	0.0472 (16)	0.061 (11)	−0.0053 (12)	0.019 (3)	−0.002 (3)
C11	0.0519 (17)	0.0476 (17)	0.059 (12)	−0.0070 (12)	0.018 (3)	−0.003 (3)
C12	0.0464 (18)	0.0528 (18)	0.036 (11)	−0.0027 (13)	0.001 (3)	−0.003 (3)
C13	0.0301 (15)	0.0483 (17)	0.041 (10)	−0.0011 (12)	0.003 (3)	−0.006 (3)

Geometric parameters (Å, º)

N1—N2	1.358 (7)	C19—C18	1.382 (3)
N1—C3	1.399 (7)	C18—H18	0.9300
N1—C14	1.435 (3)	C18—C17	1.369 (5)
N2—C1	1.346 (4)	C17—H17	0.9300
N3—C1	1.325 (6)	C17—C16	1.370 (5)
N3—C2	1.373 (7)	C16—H16	0.9300
C1—C8	1.483 (7)	C16—C15	1.390 (3)
C2—C7	1.381 (7)	C15—H15	0.9300
C2—C3	1.423 (5)	C8—C9	1.396 (4)
C7—H7	0.9300	C8—C13	1.383 (7)
C7—C6	1.361 (8)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.379 (8)
C6—C5	1.399 (4)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.366 (7)
C5—C4	1.373 (6)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.378 (4)
C4—C3	1.385 (8)	C12—H12	0.9300
C14—C19	1.371 (5)	C12—C13	1.372 (8)
C14—C15	1.370 (4)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	123.2 (3)	C18—C19—H19	120.1
N2—N1—C14	113.9 (5)	C19—C18—H18	120.1
C3—N1—C14	122.6 (5)	C17—C18—C19	119.8 (3)
C1—N2—N1	116.0 (5)	C17—C18—H18	120.1
C1—N3—C2	116.8 (4)	C18—C17—H17	119.8
N2—C1—C8	114.6 (5)	C18—C17—C16	120.4 (3)
N3—C1—N2	126.9 (6)	C16—C17—H17	119.8
N3—C1—C8	118.5 (3)	C17—C16—H16	119.9
N3—C2—C7	120.2 (4)	C17—C16—C15	120.2 (3)
N3—C2—C3	121.6 (5)	C15—C16—H16	119.9
C7—C2—C3	118.2 (6)	C14—C15—C16	119.0 (3)
C2—C7—H7	119.4	C14—C15—H15	120.5
C6—C7—C2	121.1 (4)	C16—C15—H15	120.5
C6—C7—H7	119.4	C9—C8—C1	119.2 (5)
C7—C6—H6	119.5	C13—C8—C1	122.3 (3)
C7—C6—C5	121.1 (5)	C13—C8—C9	118.5 (6)
C5—C6—H6	119.5	C8—C9—H9	120.1
C6—C5—H5	120.5	C10—C9—C8	119.8 (5)
C4—C5—C6	119.0 (5)	C10—C9—H9	120.1
C4—C5—H5	120.5	C9—C10—H10	119.5
C5—C4—H4	119.6	C11—C10—C9	121.0 (3)
C5—C4—C3	120.7 (3)	C11—C10—H10	119.5
C3—C4—H4	119.6	C10—C11—H11	120.2
N1—C3—C2	115.3 (6)	C10—C11—C12	119.7 (6)
C4—C3—N1	124.7 (3)	C12—C11—H11	120.2
C4—C3—C2	119.9 (5)	C11—C12—H12	120.0
C19—C14—N1	120.3 (3)	C13—C12—C11	120.0 (6)
C15—C14—N1	118.8 (3)	C13—C12—H12	120.0
C15—C14—C19	120.9 (2)	C8—C13—H13	119.5
C14—C19—H19	120.1	C12—C13—C8	121.1 (4)
C14—C19—C18	119.8 (3)	C12—C13—H13	119.5
N1—N2—C1—N3	1.1 (4)	C7—C6—C5—C4	0.0 (5)
N1—N2—C1—C8	−179.2 (2)	C6—C5—C4—C3	0.3 (4)
N1—C14—C19—C18	179.6 (5)	C5—C4—C3—N1	178.0 (2)
N1—C14—C15—C16	−179.8 (4)	C5—C4—C3—C2	0.0 (5)
N2—N1—C3—C2	4.0 (4)	C3—N1—N2—C1	−4.4 (4)
N2—N1—C3—C4	−174.0 (3)	C3—N1—C14—C19	57.5 (5)
N2—N1—C14—C19	−128.6 (4)	C3—N1—C14—C15	−123.8 (4)
N2—N1—C14—C15	50.1 (5)	C3—C2—C7—C6	0.9 (5)
N2—C1—C8—C9	172.4 (2)	C14—N1—N2—C1	−178.26 (18)
N2—C1—C8—C13	−8.4 (4)	C14—N1—C3—C2	177.4 (2)
N3—C1—C8—C9	−7.9 (4)	C14—N1—C3—C4	−0.6 (5)
N3—C1—C8—C13	171.2 (2)	C14—C19—C18—C17	−0.6 (7)
N3—C2—C7—C6	−177.3 (3)	C19—C14—C15—C16	−1.1 (7)
N3—C2—C3—N1	−0.5 (4)	C19—C18—C17—C16	0.3 (7)
N3—C2—C3—C4	177.6 (3)	C18—C17—C16—C15	−0.5 (8)
C1—N3—C2—C7	175.8 (2)	C17—C16—C15—C14	0.9 (7)
C1—N3—C2—C3	−2.3 (4)	C15—C14—C19—C18	1.0 (7)
C1—C8—C9—C10	179.1 (3)	C8—C9—C10—C11	0.0 (5)
C1—C8—C13—C12	−178.9 (3)	C9—C8—C13—C12	0.2 (5)
C2—N3—C1—N2	2.1 (4)	C9—C10—C11—C12	0.1 (5)
C2—N3—C1—C8	−177.5 (2)	C10—C11—C12—C13	0.0 (5)
C2—C7—C6—C5	−0.6 (5)	C11—C12—C13—C8	−0.2 (5)
C7—C2—C3—N1	−178.7 (2)	C13—C8—C9—C10	−0.1 (4)
C7—C2—C3—C4	−0.6 (4)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20034_0m_0p8792GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.437 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.3374 (18) Å	Cell parameters from 1054 reflections
b = 6.629 (3) Å	θ = 3.5–23.9°
c = 19.466 (4) Å	µ = 0.09 mm^−1
β = 99.780 (8)°	T = 300 K
V = 1314.5 (6) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	846 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	479 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.072
Detector resolution: 7.9 pixels mm^-1	θmax = 26.2°, θmin = 2.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1200 before and 0.0476 after correction. The Ratio of minimum to maximum transmission is 0.8464. The λ/2 correction factor is Not present.	k = −2→2
Tmin = 0.631, Tmax = 0.745	l = −22→23
4283 measured reflections

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)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0553P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
846 reflections	Δρmax = 0.14 e Å^−3
194 parameters	Δρmin = −0.14 e Å^−3
249 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. High pressure data collection in a diamond anvil cell. 0.8792 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ··· 6 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 249 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 65 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 9 Note PLAT951_ALERT_5_G Calculated (ThMax) and CIF-Reported Kmax Differ 6 Units PLAT957_ALERT_1_G Calculated (ThMax) and Actual (FCF) Kmax Differ 6 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4734 (2)	0.7083 (12)	0.65824 (14)	0.036 (4)
N2	0.4422 (2)	0.7033 (11)	0.72398 (13)	0.032 (5)
N3	0.2145 (2)	0.6922 (13)	0.67380 (14)	0.055 (6)
C1	0.3139 (3)	0.6983 (14)	0.72633 (17)	0.035 (6)
C2	0.2476 (3)	0.6885 (15)	0.60787 (17)	0.027 (6)
C7	0.1512 (3)	0.6700 (16)	0.54981 (18)	0.043 (6)
H7	0.063781	0.664927	0.555527	0.052*
C6	0.1808 (3)	0.6588 (15)	0.48406 (19)	0.038 (6)
H6	0.114319	0.647931	0.445543	0.046*
C5	0.3117 (3)	0.6640 (15)	0.47556 (18)	0.053 (6)
H5	0.332531	0.651830	0.431112	0.063*
C4	0.4102 (3)	0.6867 (15)	0.53150 (17)	0.040 (6)
H4	0.496965	0.695513	0.524831	0.048*
C3	0.3802 (3)	0.6967 (15)	0.59848 (18)	0.023 (6)
C14	0.6129 (3)	0.7091 (12)	0.65846 (19)	0.037 (4)
C19	0.6664 (3)	0.8514 (13)	0.62066 (18)	0.044 (4)
H19	0.613362	0.947603	0.594959	0.052*
C18	0.8008 (3)	0.8502 (14)	0.62117 (19)	0.050 (4)
H18	0.838079	0.947232	0.596076	0.061*
C17	0.8783 (3)	0.7082 (13)	0.6581 (2)	0.052 (4)
H17	0.968160	0.707166	0.657685	0.063*
C16	0.8236 (3)	0.5653 (14)	0.69633 (19)	0.055 (5)
H16	0.876413	0.468576	0.721900	0.066*
C15	0.6887 (3)	0.5673 (14)	0.69628 (19)	0.044 (4)
H15	0.651014	0.472242	0.721941	0.053*
C8	0.2824 (3)	0.6925 (15)	0.79815 (17)	0.024 (5)
C9	0.1516 (3)	0.7109 (16)	0.80715 (18)	0.0324 (10)*
H9	0.085238	0.724259	0.768663	0.039*
C10	0.1215 (3)	0.7091 (18)	0.87400 (18)	0.040 (6)
H10	0.034833	0.725103	0.880177	0.047*
C11	0.2173 (3)	0.6842 (17)	0.9305 (2)	0.043 (6)
H11	0.195668	0.679634	0.974985	0.052*
C12	0.3467 (3)	0.6655 (18)	0.92196 (19)	0.042 (6)
H12	0.412280	0.648713	0.960608	0.050*
C13	0.3785 (3)	0.6720 (15)	0.85601 (18)	0.027 (5)
H13	0.465933	0.662324	0.850567	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0232 (12)	0.057 (14)	0.0271 (19)	0.000 (2)	0.0039 (13)	0.002 (3)
N2	0.0290 (13)	0.042 (15)	0.0274 (19)	−0.002 (2)	0.0069 (13)	0.000 (3)
N3	0.0281 (13)	0.114 (18)	0.0242 (19)	0.001 (3)	0.0032 (13)	0.000 (3)
C1	0.0271 (15)	0.047 (19)	0.029 (2)	0.002 (3)	0.0003 (16)	−0.002 (4)
C2	0.0314 (17)	0.02 (2)	0.031 (2)	0.002 (3)	0.0048 (17)	0.009 (4)
C7	0.0247 (15)	0.07 (2)	0.035 (2)	0.002 (3)	0.0001 (16)	0.005 (4)
C6	0.0384 (17)	0.041 (19)	0.033 (2)	−0.006 (3)	0.0007 (18)	−0.001 (4)
C5	0.0425 (17)	0.09 (2)	0.026 (2)	0.005 (3)	0.0053 (17)	0.005 (4)
C4	0.0318 (16)	0.06 (2)	0.032 (2)	0.004 (3)	0.0070 (17)	0.001 (4)
C3	0.0267 (15)	0.01 (2)	0.035 (2)	−0.001 (3)	0.0047 (16)	−0.001 (4)
C14	0.0250 (15)	0.063 (13)	0.024 (2)	0.004 (3)	0.0052 (17)	−0.001 (4)
C19	0.0337 (16)	0.062 (14)	0.035 (3)	0.001 (3)	0.0074 (18)	0.000 (4)
C18	0.0338 (17)	0.084 (14)	0.035 (3)	−0.013 (3)	0.010 (2)	−0.004 (4)
C17	0.0244 (15)	0.099 (14)	0.034 (3)	0.002 (3)	0.0074 (18)	−0.004 (4)
C16	0.0341 (17)	0.093 (14)	0.037 (3)	0.016 (3)	0.0045 (18)	0.009 (4)
C15	0.0357 (17)	0.070 (14)	0.027 (3)	0.006 (3)	0.005 (2)	0.006 (4)
C8	0.0310 (16)	0.008 (16)	0.034 (2)	−0.004 (3)	0.0084 (16)	−0.006 (4)
C10	0.0366 (17)	0.043 (19)	0.043 (3)	−0.008 (4)	0.0164 (18)	−0.010 (4)
C11	0.0537 (19)	0.04 (2)	0.035 (3)	−0.008 (4)	0.0156 (18)	−0.007 (4)
C12	0.0439 (18)	0.043 (19)	0.037 (3)	−0.003 (4)	0.0043 (18)	−0.002 (4)
C13	0.0298 (16)	0.015 (16)	0.037 (2)	0.005 (3)	0.0045 (16)	0.002 (4)

Geometric parameters (Å, º)

N1—N2	1.373 (3)	C19—C18	1.387 (4)
N1—C3	1.381 (4)	C18—H18	0.9300
N1—C14	1.441 (3)	C18—C17	1.360 (7)
N2—C1	1.335 (3)	C17—H17	0.9300
N3—C1	1.321 (4)	C17—C16	1.383 (7)
N3—C2	1.383 (4)	C16—H16	0.9300
C1—C8	1.488 (4)	C16—C15	1.394 (4)
C2—C7	1.379 (4)	C15—H15	0.9300
C2—C3	1.414 (4)	C8—C9	1.399 (4)
C7—H7	0.9300	C8—C13	1.376 (4)
C7—C6	1.367 (4)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.388 (4)
C6—C5	1.391 (4)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.360 (5)
C5—C4	1.367 (4)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.382 (4)
C4—C3	1.392 (4)	C12—H12	0.9300
C14—C19	1.369 (7)	C12—C13	1.379 (4)
C14—C15	1.358 (7)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	122.9 (2)	C18—C19—H19	120.4
N2—N1—C14	113.0 (3)	C19—C18—H18	119.8
C3—N1—C14	123.9 (2)	C17—C18—C19	120.5 (5)
C1—N2—N1	115.2 (3)	C17—C18—H18	119.8
C1—N3—C2	115.9 (2)	C18—C17—H17	120.0
N2—C1—C8	114.2 (3)	C18—C17—C16	120.0 (3)
N3—C1—N2	128.3 (3)	C16—C17—H17	120.0
N3—C1—C8	117.5 (2)	C17—C16—H16	120.2
N3—C2—C3	121.1 (3)	C17—C16—C15	119.6 (5)
C7—C2—N3	120.3 (2)	C15—C16—H16	120.2
C7—C2—C3	118.6 (3)	C14—C15—C16	119.5 (5)
C2—C7—H7	119.1	C14—C15—H15	120.3
C6—C7—C2	121.8 (3)	C16—C15—H15	120.3
C6—C7—H7	119.1	C9—C8—C1	119.0 (3)
C7—C6—H6	120.4	C13—C8—C1	121.9 (2)
C7—C6—C5	119.1 (3)	C13—C8—C9	119.0 (3)
C5—C6—H6	120.4	C8—C9—H9	120.3
C6—C5—H5	119.5	C10—C9—C8	119.5 (3)
C4—C5—C6	121.0 (3)	C10—C9—H9	120.3
C4—C5—H5	119.5	C9—C10—H10	119.6
C5—C4—H4	120.1	C11—C10—C9	120.8 (3)
C5—C4—C3	119.8 (3)	C11—C10—H10	119.6
C3—C4—H4	120.1	C10—C11—H11	120.0
N1—C3—C2	116.5 (3)	C10—C11—C12	120.0 (3)
N1—C3—C4	123.8 (2)	C12—C11—H11	120.0
C4—C3—C2	119.6 (3)	C11—C12—H12	120.0
C19—C14—N1	119.8 (5)	C13—C12—C11	119.9 (4)
C15—C14—N1	119.0 (5)	C13—C12—H12	120.0
C15—C14—C19	121.3 (3)	C8—C13—C12	120.8 (3)
C14—C19—H19	120.4	C8—C13—H13	119.6
C14—C19—C18	119.2 (5)	C12—C13—H13	119.6
N1—N2—C1—N3	1.9 (12)	C7—C6—C5—C4	−2.2 (13)
N1—N2—C1—C8	179.8 (9)	C6—C5—C4—C3	2.6 (14)
N1—C14—C19—C18	−179.8 (5)	C5—C4—C3—N1	176.3 (9)
N1—C14—C15—C16	179.4 (5)	C5—C4—C3—C2	−1.6 (15)
N2—N1—C3—C2	2.8 (13)	C3—N1—N2—C1	−3.7 (11)
N2—N1—C3—C4	−175.2 (9)	C3—N1—C14—C19	56.0 (10)
N2—N1—C14—C19	−129.1 (6)	C3—N1—C14—C15	−123.8 (8)
N2—N1—C14—C15	51.1 (9)	C3—C2—C7—C6	0.2 (14)
N2—C1—C8—C9	172.5 (7)	C14—N1—N2—C1	−178.7 (6)
N2—C1—C8—C13	−6.7 (12)	C14—N1—C3—C2	177.2 (8)
N3—C1—C8—C9	−9.3 (15)	C14—N1—C3—C4	−0.7 (14)
N3—C1—C8—C13	171.5 (7)	C14—C19—C18—C17	0.7 (8)
N3—C2—C7—C6	−177.7 (10)	C19—C14—C15—C16	−0.4 (9)
N3—C2—C3—N1	0.1 (14)	C19—C18—C17—C16	−0.9 (8)
N3—C2—C3—C4	178.1 (10)	C18—C17—C16—C15	0.4 (8)
C1—N3—C2—C7	176.1 (9)	C17—C16—C15—C14	0.3 (9)
C1—N3—C2—C3	−1.7 (13)	C15—C14—C19—C18	0.0 (8)
C1—C8—C9—C10	−178.9 (11)	C8—C9—C10—C11	−1.8 (16)
C1—C8—C13—C12	−179.5 (11)	C9—C8—C13—C12	1.3 (14)
C2—N3—C1—N2	0.7 (13)	C9—C10—C11—C12	1.7 (16)
C2—N3—C1—C8	−177.1 (9)	C10—C11—C12—C13	−0.1 (16)
C2—C7—C6—C5	0.7 (14)	C11—C12—C13—C8	−1.4 (15)
C7—C2—C3—N1	−177.8 (8)	C13—C8—C9—C10	0.3 (15)
C7—C2—C3—C4	0.2 (14)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20041_0m_1p0994GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.456 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.3045 (6) Å	Cell parameters from 2249 reflections
b = 6.5805 (4) Å	θ = 3.3–24.1°
c = 19.408 (2) Å	µ = 0.09 mm^−1
β = 99.823 (6)°	T = 271 K
V = 1296.7 (2) Å^3	Block, clear dark brown
Z = 4	0.18 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	888 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	613 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.038
Detector resolution: 7.9 pixels mm^-1	θmax = 26.4°, θmin = 2.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0580 before and 0.0448 after correction. The Ratio of minimum to maximum transmission is 0.8904. The λ/2 correction factor is Not present.	k = −8→8
Tmin = 0.664, Tmax = 0.745	l = −8→8
7436 measured reflections

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)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0503P)^2 + 0.1084P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
888 reflections	Δρmax = 0.08 e Å^−3
199 parameters	Δρmin = −0.07 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 1.0994 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ··· -3 Units PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 59 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4740 (2)	0.7069 (3)	0.6589 (3)	0.030 (3)
N2	0.4428 (2)	0.7000 (3)	0.7241 (3)	0.030 (3)
N3	0.2143 (2)	0.6894 (3)	0.6739 (3)	0.031 (3)
C1	0.3133 (3)	0.6938 (3)	0.7270 (4)	0.026 (3)
C2	0.2466 (3)	0.6863 (4)	0.6083 (4)	0.028 (3)
C7	0.1497 (3)	0.6684 (4)	0.5500 (4)	0.032 (3)
H7	0.061914	0.662853	0.555599	0.038*
C6	0.1801 (3)	0.6586 (4)	0.4844 (4)	0.035 (3)
H6	0.112831	0.646908	0.445993	0.042*
C5	0.3113 (2)	0.6660 (3)	0.4741 (3)	0.036 (3)
H5	0.331602	0.658534	0.429327	0.043*
C4	0.4099 (3)	0.6845 (4)	0.5316 (4)	0.031 (3)
H4	0.497389	0.689566	0.525467	0.037*
C3	0.3797 (3)	0.6954 (4)	0.5980 (4)	0.028 (3)
C14	0.61292 (18)	0.7075 (3)	0.6582 (3)	0.022 (3)
C19	0.66735 (19)	0.8528 (3)	0.6210 (3)	0.033 (3)
H19	0.614204	0.950976	0.595791	0.039*
C18	0.8011 (2)	0.8521 (4)	0.6212 (3)	0.041 (4)
H18	0.838283	0.949621	0.595847	0.049*
C17	0.8788 (2)	0.7093 (4)	0.6583 (3)	0.045 (4)
H17	0.968914	0.709068	0.657914	0.054*
C16	0.8253 (2)	0.5650 (4)	0.6965 (3)	0.045 (4)
H16	0.879261	0.468329	0.721968	0.054*
C15	0.69047 (18)	0.5641 (3)	0.6968 (3)	0.035 (3)
H15	0.653430	0.467988	0.722729	0.042*
C8	0.2826 (3)	0.6910 (3)	0.7990 (4)	0.027 (3)
C9	0.1512 (2)	0.7100 (3)	0.8079 (3)	0.037 (3)
H9	0.084966	0.725356	0.769213	0.045*
C10	0.1206 (3)	0.7060 (4)	0.8740 (3)	0.041 (3)
H10	0.033186	0.718362	0.879708	0.049*
C11	0.2169 (3)	0.6840 (3)	0.9319 (3)	0.042 (3)
H11	0.194892	0.681407	0.976377	0.050*
C12	0.3467 (3)	0.6657 (4)	0.9233 (4)	0.040 (3)
H12	0.412673	0.650621	0.962171	0.048*
C13	0.3782 (3)	0.6700 (4)	0.8573 (4)	0.033 (3)
H13	0.465876	0.658484	0.851936	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0211 (13)	0.0382 (11)	0.034 (9)	−0.0002 (8)	0.011 (2)	0.001 (2)
N2	0.0186 (13)	0.0372 (10)	0.033 (9)	−0.0017 (7)	0.005 (2)	−0.001 (2)
N3	0.0220 (14)	0.0330 (10)	0.036 (9)	0.0017 (8)	−0.002 (3)	0.001 (2)
C1	0.0219 (15)	0.0213 (11)	0.034 (9)	−0.0003 (9)	0.003 (3)	0.002 (2)
C2	0.0242 (17)	0.0253 (11)	0.035 (9)	0.0002 (9)	0.005 (3)	−0.001 (3)
C7	0.0193 (14)	0.0381 (13)	0.035 (10)	0.0005 (10)	−0.002 (3)	0.003 (3)
C6	0.0312 (16)	0.0394 (13)	0.034 (10)	0.0018 (10)	0.001 (3)	0.000 (3)
C5	0.0340 (15)	0.0428 (13)	0.030 (10)	0.0028 (10)	0.005 (3)	0.000 (2)
C4	0.0238 (15)	0.0391 (13)	0.030 (9)	0.0014 (10)	0.005 (3)	−0.001 (3)
C3	0.0228 (16)	0.0275 (11)	0.035 (9)	0.0012 (9)	0.004 (3)	−0.004 (2)
C14	0.0184 (10)	0.0345 (11)	0.013 (9)	−0.0001 (8)	0.003 (2)	−0.0035 (17)
C19	0.0283 (12)	0.0415 (13)	0.028 (11)	−0.0013 (9)	0.003 (2)	−0.0020 (19)
C18	0.0285 (13)	0.0650 (16)	0.031 (12)	−0.0139 (10)	0.008 (2)	−0.002 (2)
C17	0.0203 (12)	0.089 (2)	0.027 (12)	0.0004 (12)	0.004 (2)	−0.003 (3)
C16	0.0316 (13)	0.0745 (18)	0.026 (12)	0.0164 (12)	−0.004 (3)	0.001 (3)
C15	0.0305 (12)	0.0502 (14)	0.025 (10)	0.0038 (9)	0.007 (2)	0.004 (2)
C8	0.0230 (15)	0.0243 (11)	0.034 (9)	−0.0004 (9)	0.005 (3)	−0.001 (2)
C9	0.0248 (15)	0.0333 (12)	0.054 (10)	−0.0031 (9)	0.007 (3)	0.004 (3)
C10	0.0280 (15)	0.0390 (13)	0.059 (11)	−0.0044 (10)	0.015 (3)	0.001 (2)
C11	0.0446 (16)	0.0373 (13)	0.048 (11)	−0.0054 (10)	0.019 (3)	−0.001 (2)
C12	0.0401 (18)	0.0399 (14)	0.039 (10)	−0.0038 (11)	0.004 (3)	−0.003 (3)
C13	0.0228 (15)	0.0369 (13)	0.038 (10)	0.0001 (10)	0.001 (3)	−0.002 (3)

Geometric parameters (Å, º)

N1—N2	1.358 (7)	C19—C18	1.377 (3)
N1—C3	1.398 (7)	C18—H18	0.9300
N1—C14	1.434 (3)	C18—C17	1.359 (5)
N2—C1	1.346 (3)	C17—H17	0.9300
N3—C1	1.321 (6)	C17—C16	1.375 (5)
N3—C2	1.369 (7)	C16—H16	0.9300
C1—C8	1.486 (7)	C16—C15	1.391 (3)
C2—C7	1.380 (7)	C15—H15	0.9300
C2—C3	1.421 (5)	C8—C9	1.399 (4)
C7—H7	0.9300	C8—C13	1.374 (7)
C7—C6	1.364 (8)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.372 (7)
C6—C5	1.401 (4)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.374 (7)
C5—C4	1.380 (6)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.380 (4)
C4—C3	1.378 (7)	C12—H12	0.9300
C14—C19	1.374 (4)	C12—C13	1.376 (8)
C14—C15	1.373 (4)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	123.0 (3)	C18—C19—H19	120.2
N2—N1—C14	113.8 (5)	C19—C18—H18	119.9
C3—N1—C14	122.9 (5)	C17—C18—C19	120.2 (3)
C1—N2—N1	115.7 (5)	C17—C18—H18	119.9
C1—N3—C2	116.6 (4)	C18—C17—H17	119.7
N2—C1—C8	114.3 (5)	C18—C17—C16	120.6 (2)
N3—C1—N2	127.4 (6)	C16—C17—H17	119.7
N3—C1—C8	118.3 (3)	C17—C16—H16	120.1
N3—C2—C7	120.4 (3)	C17—C16—C15	119.8 (3)
N3—C2—C3	121.6 (5)	C15—C16—H16	120.1
C7—C2—C3	117.9 (6)	C14—C15—C16	118.9 (3)
C2—C7—H7	119.3	C14—C15—H15	120.5
C6—C7—C2	121.4 (4)	C16—C15—H15	120.5
C6—C7—H7	119.3	C9—C8—C1	118.7 (5)
C7—C6—H6	119.6	C13—C8—C1	122.5 (3)
C7—C6—C5	120.8 (5)	C13—C8—C9	118.8 (6)
C5—C6—H6	119.6	C8—C9—H9	120.2
C6—C5—H5	120.5	C10—C9—C8	119.6 (5)
C4—C5—C6	118.9 (5)	C10—C9—H9	120.2
C4—C5—H5	120.5	C9—C10—H10	119.4
C5—C4—H4	119.8	C9—C10—C11	121.2 (3)
C3—C4—C5	120.5 (3)	C11—C10—H10	119.4
C3—C4—H4	119.8	C10—C11—H11	120.3
N1—C3—C2	115.5 (6)	C10—C11—C12	119.4 (5)
C4—C3—N1	123.9 (3)	C12—C11—H11	120.3
C4—C3—C2	120.5 (5)	C11—C12—H12	120.1
C19—C14—N1	120.3 (3)	C13—C12—C11	119.8 (5)
C15—C14—N1	118.8 (3)	C13—C12—H12	120.1
C15—C14—C19	120.86 (19)	C8—C13—C12	121.3 (4)
C14—C19—H19	120.2	C8—C13—H13	119.4
C14—C19—C18	119.6 (3)	C12—C13—H13	119.4
N1—N2—C1—N3	1.5 (4)	C7—C6—C5—C4	−0.4 (4)
N1—N2—C1—C8	−178.7 (2)	C6—C5—C4—C3	0.0 (4)
N1—C14—C19—C18	179.6 (4)	C5—C4—C3—N1	177.62 (18)
N1—C14—C15—C16	−179.7 (4)	C5—C4—C3—C2	0.5 (4)
N2—N1—C3—C2	3.1 (3)	C3—N1—N2—C1	−3.9 (4)
N2—N1—C3—C4	−174.2 (3)	C3—N1—C14—C19	57.1 (4)
N2—N1—C14—C19	−128.5 (4)	C3—N1—C14—C15	−124.6 (4)
N2—N1—C14—C15	49.8 (4)	C3—C2—C7—C6	0.3 (4)
N2—C1—C8—C9	172.14 (18)	C14—N1—N2—C1	−178.30 (16)
N2—C1—C8—C13	−8.0 (4)	C14—N1—C3—C2	176.96 (19)
N3—C1—C8—C9	−8.1 (3)	C14—N1—C3—C4	−0.3 (4)
N3—C1—C8—C13	171.82 (19)	C14—C19—C18—C17	−0.4 (6)
N3—C2—C7—C6	−177.9 (3)	C19—C14—C15—C16	−1.5 (6)
N3—C2—C3—N1	0.2 (4)	C19—C18—C17—C16	−0.5 (7)
N3—C2—C3—C4	177.6 (3)	C18—C17—C16—C15	0.4 (7)
C1—N3—C2—C7	175.79 (18)	C17—C16—C15—C14	0.6 (6)
C1—N3—C2—C3	−2.4 (4)	C15—C14—C19—C18	1.4 (6)
C1—C8—C9—C10	179.4 (3)	C8—C9—C10—C11	0.2 (4)
C1—C8—C13—C12	−179.3 (2)	C9—C8—C13—C12	0.6 (4)
C2—N3—C1—N2	1.6 (4)	C9—C10—C11—C12	0.0 (4)
C2—N3—C1—C8	−178.2 (2)	C10—C11—C12—C13	0.1 (4)
C2—C7—C6—C5	0.2 (4)	C11—C12—C13—C8	−0.4 (5)
C7—C2—C3—N1	−178.0 (2)	C13—C8—C9—C10	−0.5 (4)
C7—C2—C3—C4	−0.7 (4)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (sp20043_0m_1p3749GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.480 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2760 (5) Å	Cell parameters from 2348 reflections
b = 6.5173 (3) Å	θ = 3.3–24.8°
c = 19.3323 (19) Å	µ = 0.09 mm^−1
β = 99.826 (5)°	T = 271 K
V = 1275.73 (15) Å^3	Block, clear dark brown
Z = 4	0.18 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	878 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	623 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.033
Detector resolution: 7.9 pixels mm^-1	θmax = 26.3°, θmin = 2.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0528 before and 0.0392 after correction. The Ratio of minimum to maximum transmission is 0.9029. The λ/2 correction factor is Not present.	k = −8→8
Tmin = 0.673, Tmax = 0.745	l = −8→8
7309 measured reflections

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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0532P)^2 + 0.0955P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
878 reflections	Δρmax = 0.07 e Å^−3
199 parameters	Δρmin = −0.08 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 1.3749 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 62 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4740 (2)	0.7051 (3)	0.6592 (3)	0.033 (3)
N2	0.4427 (2)	0.6972 (3)	0.7246 (3)	0.032 (3)
N3	0.2138 (2)	0.6872 (3)	0.6746 (3)	0.028 (3)
C1	0.3131 (3)	0.6913 (3)	0.7280 (4)	0.024 (3)
C2	0.2464 (3)	0.6839 (3)	0.6087 (4)	0.025 (3)
C7	0.1492 (3)	0.6675 (3)	0.5500 (4)	0.028 (3)
H7	0.061170	0.662991	0.555672	0.034*
C6	0.1792 (3)	0.6575 (4)	0.4839 (4)	0.033 (3)
H6	0.111843	0.644938	0.445393	0.040*
C5	0.3106 (2)	0.6662 (3)	0.4738 (3)	0.034 (3)
H5	0.330886	0.659318	0.428820	0.041*
C4	0.4096 (3)	0.6849 (4)	0.5311 (4)	0.032 (3)
H4	0.497156	0.691484	0.524647	0.038*
C3	0.3799 (3)	0.6940 (3)	0.5979 (4)	0.028 (3)
C14	0.61350 (18)	0.7055 (3)	0.6587 (3)	0.022 (3)
C19	0.66769 (19)	0.8527 (3)	0.6212 (3)	0.030 (3)
H19	0.614148	0.951774	0.596084	0.036*
C18	0.8019 (2)	0.8525 (4)	0.6212 (3)	0.039 (4)
H18	0.838990	0.951456	0.595903	0.046*
C17	0.8802 (2)	0.7074 (4)	0.6584 (3)	0.044 (3)
H17	0.970549	0.707151	0.657893	0.053*
C16	0.8264 (2)	0.5613 (4)	0.6966 (3)	0.044 (4)
H16	0.880485	0.463217	0.722020	0.052*
C15	0.69115 (18)	0.5604 (3)	0.6972 (3)	0.032 (3)
H15	0.654071	0.463192	0.723216	0.038*
C8	0.2819 (2)	0.6883 (3)	0.7999 (3)	0.025 (3)
C9	0.1504 (2)	0.7069 (3)	0.8085 (3)	0.034 (3)
H9	0.083882	0.720897	0.769583	0.041*
C10	0.1201 (3)	0.7044 (4)	0.8752 (3)	0.037 (3)
H10	0.032525	0.717800	0.881015	0.045*
C11	0.2165 (2)	0.6826 (3)	0.9330 (3)	0.039 (3)
H11	0.194585	0.680398	0.977719	0.047*
C12	0.3469 (3)	0.6640 (4)	0.9244 (4)	0.034 (3)
H12	0.413100	0.648774	0.963366	0.041*
C13	0.3786 (3)	0.6679 (3)	0.8581 (3)	0.029 (3)
H13	0.466455	0.656622	0.852559	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0192 (12)	0.0380 (11)	0.043 (9)	−0.0002 (8)	0.010 (2)	0.001 (2)
N2	0.0191 (12)	0.0358 (11)	0.043 (9)	−0.0017 (7)	0.006 (2)	−0.001 (2)
N3	0.0200 (13)	0.0317 (11)	0.032 (8)	0.0014 (8)	0.000 (2)	0.002 (2)
C1	0.0199 (13)	0.0216 (11)	0.030 (8)	0.0002 (8)	0.001 (3)	−0.001 (2)
C2	0.0226 (16)	0.0243 (12)	0.030 (9)	0.0013 (9)	0.006 (3)	−0.001 (3)
C7	0.0194 (14)	0.0349 (13)	0.029 (9)	0.0014 (9)	0.001 (2)	−0.001 (3)
C6	0.0320 (15)	0.0363 (13)	0.031 (10)	0.0017 (10)	0.006 (3)	−0.002 (3)
C5	0.0313 (13)	0.0400 (13)	0.030 (10)	0.0012 (9)	0.004 (2)	0.000 (2)
C4	0.0232 (15)	0.0383 (14)	0.034 (9)	0.0006 (10)	0.007 (3)	−0.001 (3)
C3	0.0225 (15)	0.0255 (12)	0.038 (9)	0.0002 (9)	0.006 (3)	−0.003 (2)
C14	0.0177 (10)	0.0359 (12)	0.014 (9)	0.0007 (8)	0.002 (2)	−0.0012 (18)
C19	0.0264 (11)	0.0379 (13)	0.025 (10)	−0.0006 (8)	0.003 (2)	−0.0005 (18)
C18	0.0277 (12)	0.0609 (16)	0.029 (12)	−0.0108 (10)	0.009 (2)	−0.003 (2)
C17	0.0206 (11)	0.082 (2)	0.029 (11)	0.0002 (11)	0.005 (2)	−0.005 (3)
C16	0.0308 (12)	0.0687 (18)	0.030 (11)	0.0162 (11)	0.001 (2)	0.004 (3)
C15	0.0304 (11)	0.0481 (14)	0.019 (10)	0.0020 (9)	0.011 (2)	0.001 (2)
C8	0.0213 (14)	0.0229 (11)	0.029 (9)	−0.0007 (8)	0.002 (3)	0.000 (2)
C9	0.0223 (14)	0.0323 (13)	0.048 (10)	−0.0030 (8)	0.005 (3)	0.001 (2)
C10	0.0272 (14)	0.0356 (13)	0.052 (10)	−0.0026 (10)	0.016 (3)	0.002 (2)
C11	0.0427 (15)	0.0365 (13)	0.042 (10)	−0.0054 (10)	0.018 (3)	−0.001 (2)
C12	0.0370 (16)	0.0362 (14)	0.029 (10)	−0.0027 (10)	0.002 (3)	−0.003 (3)
C13	0.0229 (14)	0.0354 (13)	0.029 (9)	−0.0002 (10)	0.002 (3)	−0.001 (2)

Geometric parameters (Å, º)

N1—N2	1.358 (7)	C19—C18	1.379 (3)
N1—C3	1.397 (7)	C18—H18	0.9300
N1—C14	1.435 (3)	C18—C17	1.364 (5)
N2—C1	1.345 (3)	C17—H17	0.9300
N3—C1	1.323 (6)	C17—C16	1.378 (5)
N3—C2	1.372 (7)	C16—H16	0.9300
C1—C8	1.478 (7)	C16—C15	1.392 (3)
C2—C7	1.381 (7)	C15—H15	0.9300
C2—C3	1.424 (4)	C8—C9	1.395 (4)
C7—H7	0.9300	C8—C13	1.375 (7)
C7—C6	1.367 (8)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.377 (7)
C6—C5	1.398 (4)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.369 (7)
C5—C4	1.374 (6)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.384 (4)
C4—C3	1.379 (7)	C12—H12	0.9300
C14—C19	1.375 (4)	C12—C13	1.376 (8)
C14—C15	1.372 (4)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	123.2 (3)	C18—C19—H19	120.2
N2—N1—C14	113.7 (4)	C19—C18—H18	120.0
C3—N1—C14	122.8 (5)	C17—C18—C19	120.1 (3)
C1—N2—N1	116.1 (5)	C17—C18—H18	120.0
C1—N3—C2	116.6 (3)	C18—C17—H17	119.8
N2—C1—C8	114.9 (5)	C18—C17—C16	120.5 (2)
N3—C1—N2	127.0 (6)	C16—C17—H17	119.8
N3—C1—C8	118.1 (3)	C17—C16—H16	120.0
N3—C2—C7	120.4 (3)	C17—C16—C15	120.0 (3)
N3—C2—C3	121.9 (5)	C15—C16—H16	120.0
C7—C2—C3	117.6 (6)	C14—C15—C16	118.8 (3)
C2—C7—H7	119.2	C14—C15—H15	120.6
C6—C7—C2	121.6 (3)	C16—C15—H15	120.6
C6—C7—H7	119.2	C9—C8—C1	118.7 (5)
C7—C6—H6	119.8	C13—C8—C1	121.9 (3)
C7—C6—C5	120.4 (5)	C13—C8—C9	119.4 (6)
C5—C6—H6	119.8	C8—C9—H9	120.4
C6—C5—H5	120.3	C10—C9—C8	119.3 (5)
C4—C5—C6	119.4 (5)	C10—C9—H9	120.4
C4—C5—H5	120.3	C9—C10—H10	119.4
C5—C4—H4	119.8	C11—C10—C9	121.2 (3)
C5—C4—C3	120.4 (3)	C11—C10—H10	119.4
C3—C4—H4	119.8	C10—C11—H11	120.3
N1—C3—C2	115.1 (5)	C10—C11—C12	119.5 (5)
C4—C3—N1	124.4 (3)	C12—C11—H11	120.3
C4—C3—C2	120.5 (5)	C11—C12—H12	120.1
C19—C14—N1	120.0 (3)	C13—C12—C11	119.9 (5)
C15—C14—N1	118.9 (3)	C13—C12—H12	120.1
C15—C14—C19	121.07 (19)	C8—C13—C12	120.8 (4)
C14—C19—H19	120.2	C8—C13—H13	119.6
C14—C19—C18	119.6 (3)	C12—C13—H13	119.6
N1—N2—C1—N3	1.9 (3)	C7—C6—C5—C4	0.0 (3)
N1—N2—C1—C8	−178.5 (2)	C6—C5—C4—C3	0.4 (4)
N1—C14—C19—C18	179.7 (4)	C5—C4—C3—N1	177.45 (17)
N1—C14—C15—C16	−180.0 (4)	C5—C4—C3—C2	0.0 (4)
N2—N1—C3—C2	3.0 (3)	C3—N1—N2—C1	−4.2 (3)
N2—N1—C3—C4	−174.5 (2)	C3—N1—C14—C19	57.0 (4)
N2—N1—C14—C19	−128.8 (4)	C3—N1—C14—C15	−124.5 (4)
N2—N1—C14—C15	49.7 (4)	C3—C2—C7—C6	1.1 (4)
N2—C1—C8—C9	172.43 (17)	C14—N1—N2—C1	−178.41 (16)
N2—C1—C8—C13	−7.5 (3)	C14—N1—C3—C2	176.70 (18)
N3—C1—C8—C9	−7.8 (3)	C14—N1—C3—C4	−0.8 (4)
N3—C1—C8—C13	172.20 (18)	C14—C19—C18—C17	−0.2 (6)
N3—C2—C7—C6	−177.9 (2)	C19—C14—C15—C16	−1.5 (6)
N3—C2—C3—N1	0.6 (3)	C19—C18—C17—C16	−0.6 (7)
N3—C2—C3—C4	178.3 (3)	C18—C17—C16—C15	0.4 (7)
C1—N3—C2—C7	176.20 (17)	C17—C16—C15—C14	0.7 (6)
C1—N3—C2—C3	−2.8 (4)	C15—C14—C19—C18	1.2 (6)
C1—C8—C9—C10	−180.0 (2)	C8—C9—C10—C11	−0.4 (4)
C1—C8—C13—C12	−179.5 (2)	C9—C8—C13—C12	0.5 (4)
C2—N3—C1—N2	1.6 (4)	C9—C10—C11—C12	0.4 (4)
C2—N3—C1—C8	−178.1 (2)	C10—C11—C12—C13	0.1 (4)
C2—C7—C6—C5	−0.7 (4)	C11—C12—C13—C8	−0.6 (4)
C7—C2—C3—N1	−178.4 (2)	C13—C8—C9—C10	0.0 (3)
C7—C2—C3—C4	−0.8 (3)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (sp20035_0m_1p8162GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.508 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2411 (11) Å	Cell parameters from 1492 reflections
b = 6.4507 (6) Å	θ = 3.3–26.2°
c = 19.247 (4) Å	µ = 0.09 mm^−1
β = 99.913 (13)°	T = 295 K
V = 1252.5 (3) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	900 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	537 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.060
Detector resolution: 7.9 pixels mm^-1	θmax = 26.4°, θmin = 2.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0770 before and 0.0513 after correction. The Ratio of minimum to maximum transmission is 0.8345. The λ/2 correction factor is Not present.	k = −8→8
Tmin = 0.622, Tmax = 0.745	l = −8→8
7133 measured reflections

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)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0587P)^2 + 0.3163P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
900 reflections	Δρmax = 0.13 e Å^−3
199 parameters	Δρmin = −0.14 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 1.8162 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 53 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 5 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4743 (4)	0.7028 (6)	0.6592 (5)	0.039 (4)
N2	0.4430 (3)	0.6929 (5)	0.7252 (4)	0.037 (4)
N3	0.2133 (4)	0.6837 (5)	0.6754 (5)	0.036 (4)
C1	0.3134 (4)	0.6884 (5)	0.7286 (5)	0.030 (4)
C2	0.2452 (4)	0.6818 (6)	0.6092 (5)	0.033 (4)
C7	0.1480 (5)	0.6652 (6)	0.5500 (5)	0.034 (4)
H7	0.059594	0.659249	0.555500	0.040*
C6	0.1782 (4)	0.6572 (6)	0.4830 (5)	0.038 (4)
H6	0.110648	0.645143	0.444216	0.046*
C5	0.3099 (4)	0.6672 (5)	0.4734 (5)	0.041 (4)
H5	0.330357	0.662133	0.428182	0.049*
C4	0.4093 (5)	0.6844 (6)	0.5309 (5)	0.039 (4)
H4	0.497235	0.690418	0.524691	0.047*
C3	0.3789 (4)	0.6928 (6)	0.5980 (5)	0.035 (4)
C14	0.6139 (3)	0.7035 (5)	0.6584 (4)	0.038 (4)
C19	0.6683 (4)	0.8531 (5)	0.6214 (5)	0.039 (5)
H19	0.614517	0.953465	0.596278	0.047*
C18	0.8030 (4)	0.8540 (6)	0.6216 (5)	0.050 (6)
H18	0.840288	0.955521	0.596815	0.060*
C17	0.8814 (4)	0.7059 (7)	0.6582 (5)	0.055 (6)
H17	0.971862	0.704926	0.657253	0.066*
C16	0.8281 (4)	0.5581 (6)	0.6966 (5)	0.051 (6)
H16	0.882793	0.459479	0.722077	0.061*
C15	0.6923 (3)	0.5557 (5)	0.6972 (5)	0.040 (5)
H15	0.655306	0.456940	0.723216	0.048*
C8	0.2810 (4)	0.6841 (6)	0.8012 (5)	0.033 (4)
C9	0.1491 (4)	0.7030 (6)	0.8092 (5)	0.039 (5)
H9	0.082238	0.715055	0.770083	0.047*
C10	0.1196 (5)	0.7033 (6)	0.8768 (5)	0.041 (5)
H10	0.031774	0.718284	0.882605	0.049*
C11	0.2156 (5)	0.6822 (5)	0.9352 (5)	0.047 (5)
H11	0.193420	0.682157	0.980030	0.056*
C12	0.3467 (4)	0.6607 (6)	0.9266 (6)	0.045 (4)
H12	0.412949	0.642810	0.965766	0.054*
C13	0.3783 (5)	0.6661 (6)	0.8601 (5)	0.040 (4)
H13	0.466644	0.657340	0.854688	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.023 (2)	0.0341 (16)	0.064 (12)	0.0001 (16)	0.013 (4)	0.002 (4)
N2	0.018 (2)	0.0336 (16)	0.058 (12)	−0.0023 (14)	0.003 (4)	−0.002 (4)
N3	0.021 (2)	0.0299 (15)	0.056 (12)	0.0025 (16)	0.003 (4)	0.003 (4)
C1	0.014 (2)	0.0181 (15)	0.056 (11)	−0.0008 (16)	0.003 (4)	−0.001 (4)
C2	0.020 (3)	0.0226 (17)	0.056 (12)	−0.0008 (17)	0.001 (4)	−0.008 (5)
C7	0.019 (2)	0.0304 (19)	0.050 (13)	0.0027 (18)	0.003 (4)	0.004 (4)
C6	0.030 (3)	0.0321 (19)	0.052 (13)	−0.0026 (17)	0.008 (5)	−0.007 (4)
C5	0.031 (2)	0.0354 (19)	0.057 (13)	0.0003 (18)	0.011 (4)	0.002 (4)
C4	0.020 (2)	0.035 (2)	0.063 (13)	0.0013 (18)	0.008 (4)	−0.001 (4)
C3	0.022 (3)	0.0235 (17)	0.062 (12)	0.0008 (17)	0.012 (4)	−0.007 (4)
C14	0.018 (2)	0.0326 (18)	0.064 (14)	0.0005 (15)	0.010 (4)	−0.003 (3)
C19	0.024 (2)	0.040 (2)	0.054 (16)	−0.0008 (15)	0.008 (4)	−0.003 (3)
C18	0.029 (2)	0.057 (2)	0.066 (19)	−0.0100 (18)	0.013 (5)	−0.004 (4)
C17	0.016 (2)	0.077 (3)	0.072 (18)	−0.002 (2)	0.008 (5)	−0.009 (4)
C16	0.026 (2)	0.065 (3)	0.056 (19)	0.0134 (19)	−0.008 (5)	−0.001 (4)
C15	0.029 (2)	0.045 (2)	0.046 (16)	0.0017 (17)	0.011 (4)	0.003 (4)
C8	0.017 (2)	0.0248 (17)	0.060 (12)	−0.0026 (16)	0.011 (4)	0.004 (4)
C9	0.022 (3)	0.0313 (18)	0.064 (14)	−0.0022 (16)	0.009 (4)	−0.001 (4)
C10	0.026 (3)	0.0336 (19)	0.067 (15)	−0.0025 (19)	0.017 (5)	−0.005 (4)
C11	0.038 (3)	0.0319 (18)	0.071 (15)	−0.0038 (19)	0.011 (5)	0.001 (4)
C12	0.033 (3)	0.036 (2)	0.063 (13)	−0.0008 (18)	−0.001 (5)	0.003 (5)
C13	0.023 (3)	0.033 (2)	0.064 (13)	−0.0029 (19)	0.007 (4)	0.005 (4)

Geometric parameters (Å, º)

N1—N2	1.362 (8)	C19—C18	1.378 (5)
N1—C3	1.397 (8)	C18—H18	0.9300
N1—C14	1.433 (5)	C18—C17	1.364 (7)
N2—C1	1.340 (5)	C17—H17	0.9300
N3—C1	1.319 (7)	C17—C16	1.375 (7)
N3—C2	1.367 (8)	C16—H16	0.9300
C1—C8	1.491 (8)	C16—C15	1.393 (5)
C2—C7	1.384 (8)	C15—H15	0.9300
C2—C3	1.424 (6)	C8—C9	1.391 (5)
C7—H7	0.9300	C8—C13	1.379 (8)
C7—C6	1.376 (8)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.385 (8)
C6—C5	1.394 (6)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.367 (8)
C5—C4	1.374 (8)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.387 (5)
C4—C3	1.380 (8)	C12—H12	0.9300
C14—C19	1.373 (6)	C12—C13	1.374 (9)
C14—C15	1.380 (6)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	122.8 (4)	C18—C19—H19	120.1
N2—N1—C14	114.0 (6)	C19—C18—H18	120.1
C3—N1—C14	123.0 (6)	C17—C18—C19	119.9 (5)
C1—N2—N1	116.1 (6)	C17—C18—H18	120.1
C1—N3—C2	116.4 (5)	C18—C17—H17	119.7
N2—C1—C8	115.4 (6)	C18—C17—C16	120.7 (4)
N3—C1—N2	127.3 (7)	C16—C17—H17	119.7
N3—C1—C8	117.3 (5)	C17—C16—H16	119.9
N3—C2—C7	121.0 (5)	C17—C16—C15	120.1 (5)
N3—C2—C3	122.1 (7)	C15—C16—H16	119.9
C7—C2—C3	116.9 (7)	C14—C15—C16	118.4 (5)
C2—C7—H7	119.0	C14—C15—H15	120.8
C6—C7—C2	121.9 (5)	C16—C15—H15	120.8
C6—C7—H7	119.0	C9—C8—C1	118.6 (7)
C7—C6—H6	120.0	C13—C8—C1	121.7 (5)
C7—C6—C5	120.1 (7)	C13—C8—C9	119.6 (7)
C5—C6—H6	120.0	C8—C9—H9	120.7
C6—C5—H5	120.1	C10—C9—C8	118.5 (7)
C4—C5—C6	119.7 (7)	C10—C9—H9	120.7
C4—C5—H5	120.1	C9—C10—H10	119.0
C5—C4—H4	119.9	C11—C10—C9	121.9 (5)
C5—C4—C3	120.2 (5)	C11—C10—H10	119.0
C3—C4—H4	119.9	C10—C11—H11	120.4
N1—C3—C2	115.1 (7)	C10—C11—C12	119.1 (7)
C4—C3—N1	123.6 (5)	C12—C11—H11	120.4
C4—C3—C2	121.2 (7)	C11—C12—H12	120.1
C19—C14—N1	120.2 (4)	C13—C12—C11	119.7 (7)
C19—C14—C15	121.1 (3)	C13—C12—H12	120.1
C15—C14—N1	118.7 (4)	C8—C13—H13	119.5
C14—C19—H19	120.1	C12—C13—C8	121.0 (6)
C14—C19—C18	119.8 (5)	C12—C13—H13	119.5
N1—N2—C1—N3	3.2 (7)	C7—C6—C5—C4	0.2 (6)
N1—N2—C1—C8	−178.2 (4)	C6—C5—C4—C3	−0.3 (6)
N1—C14—C19—C18	179.2 (7)	C5—C4—C3—N1	177.6 (3)
N1—C14—C15—C16	−179.6 (7)	C5—C4—C3—C2	0.7 (7)
N2—N1—C3—C2	3.0 (7)	C3—N1—N2—C1	−4.8 (7)
N2—N1—C3—C4	−174.1 (4)	C3—N1—C14—C19	57.2 (7)
N2—N1—C14—C19	−128.6 (6)	C3—N1—C14—C15	−124.9 (6)
N2—N1—C14—C15	49.3 (7)	C3—C2—C7—C6	0.7 (7)
N2—C1—C8—C9	172.9 (3)	C14—N1—N2—C1	−179.0 (3)
N2—C1—C8—C13	−5.9 (6)	C14—N1—C3—C2	176.6 (3)
N3—C1—C8—C9	−8.4 (6)	C14—N1—C3—C4	−0.5 (7)
N3—C1—C8—C13	172.9 (3)	C14—C19—C18—C17	0.3 (11)
N3—C2—C7—C6	−178.1 (4)	C19—C14—C15—C16	−1.7 (10)
N3—C2—C3—N1	0.8 (7)	C19—C18—C17—C16	−1.6 (11)
N3—C2—C3—C4	178.0 (5)	C18—C17—C16—C15	1.3 (11)
C1—N3—C2—C7	176.4 (3)	C17—C16—C15—C14	0.4 (11)
C1—N3—C2—C3	−2.4 (7)	C15—C14—C19—C18	1.4 (10)
C1—C8—C9—C10	−178.7 (4)	C8—C9—C10—C11	−1.1 (7)
C1—C8—C13—C12	−179.5 (4)	C9—C8—C13—C12	1.8 (7)
C2—N3—C1—N2	0.4 (7)	C9—C10—C11—C12	0.3 (7)
C2—N3—C1—C8	−178.2 (3)	C10—C11—C12—C13	1.6 (6)
C2—C7—C6—C5	−0.4 (7)	C11—C12—C13—C8	−2.6 (8)
C7—C2—C3—N1	−178.0 (4)	C13—C8—C9—C10	0.1 (6)
C7—C2—C3—C4	−0.8 (7)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20049_0m_2p1201GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.525 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2225 (8) Å	Cell parameters from 2001 reflections
b = 6.4019 (5) Å	θ = 3.4–25.2°
c = 19.203 (3) Å	µ = 0.09 mm^−1
β = 99.864 (8)°	T = 291 K
V = 1238.2 (2) Å^3	Block, clear dark brown
Z = 4	0.18 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	851 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	558 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.042
Detector resolution: 7.9 pixels mm^-1	θmax = 26.3°, θmin = 2.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1040 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.8593. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.641, Tmax = 0.745	l = −8→8
6022 measured reflections

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) = 0.102	w = 1/[σ^2(Fo^2) + (0.0563P)^2 + 0.2672P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
851 reflections	Δρmax = 0.13 e Å^−3
194 parameters	Δρmin = −0.15 e Å^−3
201 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. High pressure data collection in a diamond anvil cell. 2.1201 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.17 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 201 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 52 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 2 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4741 (3)	0.6998 (4)	0.6597 (4)	0.028 (3)
N2	0.4431 (2)	0.6907 (4)	0.7259 (4)	0.028 (3)
N3	0.2127 (3)	0.6810 (4)	0.6752 (4)	0.025 (3)
C1	0.3125 (3)	0.6850 (5)	0.7291 (4)	0.022 (3)
C2	0.2453 (3)	0.6803 (5)	0.6088 (4)	0.023 (3)
C7	0.1471 (3)	0.6640 (5)	0.5499 (4)	0.027 (4)
H7	0.058687	0.658211	0.555568	0.032*
C6	0.1775 (3)	0.6564 (5)	0.4835 (4)	0.031 (4)
H6	0.109678	0.643674	0.444693	0.037*
C5	0.3093 (3)	0.6673 (4)	0.4731 (4)	0.029 (4)
H5	0.329216	0.662326	0.427669	0.035*
C4	0.4092 (3)	0.6855 (5)	0.5305 (4)	0.028 (3)
H4	0.497083	0.693883	0.523913	0.033*
C3	0.3794 (3)	0.6914 (5)	0.5981 (4)	0.025 (3)
C14	0.6144 (2)	0.7014 (4)	0.6593 (3)	0.0214 (7)*
C19	0.6684 (2)	0.8530 (4)	0.6217 (4)	0.023 (5)
H19	0.614534	0.953984	0.596516	0.027*
C18	0.8035 (3)	0.8525 (5)	0.6222 (4)	0.040 (4)
H18	0.840819	0.954470	0.597211	0.048*
C17	0.8829 (3)	0.7043 (5)	0.6588 (4)	0.039 (4)
H17	0.973634	0.704357	0.658246	0.047*
C16	0.8283 (3)	0.5545 (5)	0.6967 (4)	0.040 (4)
H16	0.882717	0.454183	0.722000	0.048*
C15	0.6925 (2)	0.5524 (4)	0.6974 (4)	0.030 (5)
H15	0.655405	0.452081	0.723129	0.036*
C8	0.2815 (3)	0.6823 (5)	0.8018 (4)	0.023 (3)
C9	0.1492 (3)	0.7013 (5)	0.8105 (4)	0.031 (4)
H9	0.082332	0.713391	0.771264	0.038*
C10	0.1182 (3)	0.7022 (5)	0.8775 (4)	0.035 (4)
H10	0.030219	0.717500	0.883344	0.042*
C11	0.2153 (3)	0.6808 (4)	0.9357 (4)	0.037 (4)
H11	0.193062	0.679663	0.980636	0.044*
C12	0.3473 (3)	0.6607 (5)	0.9275 (5)	0.033 (4)
H12	0.413763	0.645757	0.966834	0.039*
C13	0.3785 (3)	0.6632 (5)	0.8605 (4)	0.027 (4)
H13	0.466772	0.651722	0.854983	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0184 (15)	0.0363 (15)	0.034 (11)	0.0005 (11)	0.014 (3)	0.001 (3)
N2	0.0172 (14)	0.0352 (15)	0.034 (11)	−0.0022 (10)	0.011 (3)	−0.007 (3)
N3	0.0197 (16)	0.0276 (14)	0.029 (10)	0.0008 (11)	0.005 (3)	0.000 (3)
C1	0.0202 (16)	0.0168 (15)	0.028 (10)	−0.0019 (11)	0.002 (3)	−0.002 (3)
C2	0.0210 (18)	0.0211 (16)	0.030 (10)	0.0014 (12)	0.009 (3)	−0.002 (3)
C7	0.0187 (17)	0.0302 (17)	0.032 (11)	0.0020 (12)	0.003 (3)	0.001 (3)
C6	0.0269 (18)	0.0316 (18)	0.034 (11)	0.0003 (13)	0.005 (3)	−0.003 (4)
C5	0.0295 (16)	0.0346 (18)	0.025 (11)	0.0008 (12)	0.007 (3)	−0.002 (3)
C4	0.0228 (17)	0.0311 (17)	0.031 (11)	0.0013 (13)	0.009 (3)	−0.001 (4)
C3	0.0217 (18)	0.0226 (16)	0.032 (11)	0.0000 (12)	0.008 (3)	−0.008 (3)
C19	0.0258 (14)	0.0327 (18)	0.010 (15)	0.0002 (10)	0.005 (3)	−0.002 (2)
C18	0.0256 (15)	0.054 (2)	0.041 (15)	−0.0115 (13)	0.009 (3)	−0.002 (3)
C17	0.0183 (14)	0.074 (3)	0.029 (14)	0.0000 (14)	0.010 (3)	−0.005 (3)
C16	0.0291 (16)	0.063 (2)	0.028 (14)	0.0157 (14)	0.006 (3)	0.005 (3)
C15	0.0309 (15)	0.041 (2)	0.023 (15)	0.0019 (12)	0.017 (3)	0.003 (3)
C8	0.0217 (17)	0.0201 (15)	0.027 (10)	−0.0002 (12)	0.006 (3)	0.002 (3)
C9	0.0191 (16)	0.0266 (17)	0.049 (12)	−0.0020 (12)	0.008 (3)	0.000 (3)
C10	0.0253 (17)	0.0310 (18)	0.054 (12)	−0.0024 (13)	0.019 (3)	0.000 (3)
C11	0.0395 (18)	0.0299 (17)	0.047 (12)	−0.0051 (12)	0.022 (3)	−0.003 (3)
C12	0.0351 (19)	0.0320 (18)	0.031 (12)	−0.0033 (13)	0.006 (4)	−0.002 (4)
C13	0.0210 (17)	0.0312 (18)	0.028 (11)	0.0008 (13)	0.004 (3)	−0.001 (3)

Geometric parameters (Å, º)

N1—N2	1.363 (8)	C19—C18	1.379 (3)
N1—C3	1.395 (7)	C18—H18	0.9300
N1—C14	1.437 (3)	C18—C17	1.363 (6)
N2—C1	1.348 (4)	C17—H17	0.9300
N3—C1	1.324 (7)	C17—C16	1.378 (6)
N3—C2	1.371 (8)	C16—H16	0.9300
C1—C8	1.483 (8)	C16—C15	1.391 (3)
C2—C7	1.382 (7)	C15—H15	0.9300
C2—C3	1.423 (5)	C8—C9	1.396 (5)
C7—H7	0.9300	C8—C13	1.374 (7)
C7—C6	1.363 (8)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.377 (8)
C6—C5	1.397 (5)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.368 (7)
C5—C4	1.373 (7)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.391 (4)
C4—C3	1.384 (8)	C12—H12	0.9300
C14—C19	1.379 (5)	C12—C13	1.377 (8)
C14—C15	1.372 (5)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	123.4 (4)	C18—C19—H19	120.5
N2—N1—C14	113.4 (5)	C19—C18—H18	119.6
C3—N1—C14	123.0 (6)	C17—C18—C19	120.8 (4)
C1—N2—N1	115.7 (5)	C17—C18—H18	119.6
C1—N3—C2	116.8 (4)	C18—C17—H17	120.1
N2—C1—C8	114.7 (5)	C18—C17—C16	119.9 (3)
N3—C1—N2	126.9 (7)	C16—C17—H17	120.1
N3—C1—C8	118.4 (4)	C17—C16—H16	119.8
N3—C2—C7	120.3 (4)	C17—C16—C15	120.4 (4)
N3—C2—C3	121.8 (6)	C15—C16—H16	119.8
C7—C2—C3	117.9 (6)	C14—C15—C16	118.6 (4)
C2—C7—H7	119.4	C14—C15—H15	120.7
C6—C7—C2	121.3 (4)	C16—C15—H15	120.7
C6—C7—H7	119.4	C9—C8—C1	118.7 (5)
C7—C6—H6	119.6	C13—C8—C1	122.2 (4)
C7—C6—C5	120.7 (6)	C13—C8—C9	119.1 (6)
C5—C6—H6	119.6	C8—C9—H9	120.1
C6—C5—H5	120.2	C10—C9—C8	119.7 (6)
C4—C5—C6	119.5 (6)	C10—C9—H9	120.1
C4—C5—H5	120.2	C9—C10—H10	119.6
C5—C4—H4	119.9	C11—C10—C9	120.7 (4)
C5—C4—C3	120.1 (4)	C11—C10—H10	119.6
C3—C4—H4	119.9	C10—C11—H11	120.0
N1—C3—C2	115.2 (6)	C10—C11—C12	120.0 (7)
C4—C3—N1	124.3 (4)	C12—C11—H11	120.0
C4—C3—C2	120.5 (5)	C11—C12—H12	120.4
C19—C14—N1	119.8 (3)	C13—C12—C11	119.2 (6)
C15—C14—N1	118.9 (3)	C13—C12—H12	120.4
C15—C14—C19	121.3 (2)	C8—C13—C12	121.2 (4)
C14—C19—H19	120.5	C8—C13—H13	119.4
C14—C19—C18	119.0 (4)	C12—C13—H13	119.4
N1—N2—C1—N3	2.2 (5)	C7—C6—C5—C4	0.2 (5)
N1—N2—C1—C8	−178.1 (3)	C6—C5—C4—C3	0.5 (5)
N1—C14—C19—C18	179.7 (5)	C5—C4—C3—N1	176.9 (2)
N1—C14—C15—C16	179.9 (5)	C5—C4—C3—C2	−0.5 (5)
N2—N1—C3—C2	2.3 (5)	C3—N1—N2—C1	−3.7 (5)
N2—N1—C3—C4	−175.2 (3)	C3—N1—C14—C19	56.2 (6)
N2—N1—C14—C19	−128.7 (5)	C3—N1—C14—C15	−124.7 (5)
N2—N1—C14—C15	50.4 (6)	C3—C2—C7—C6	0.8 (5)
N2—C1—C8—C9	172.5 (2)	C14—N1—N2—C1	−178.8 (2)
N2—C1—C8—C13	−7.0 (5)	C14—N1—C3—C2	176.9 (3)
N3—C1—C8—C9	−7.7 (5)	C14—N1—C3—C4	−0.6 (5)
N3—C1—C8—C13	172.8 (2)	C14—C19—C18—C17	0.3 (9)
N3—C2—C7—C6	−177.9 (3)	C19—C14—C15—C16	−1.0 (8)
N3—C2—C3—N1	0.9 (4)	C19—C18—C17—C16	−0.9 (9)
N3—C2—C3—C4	178.5 (4)	C18—C17—C16—C15	0.5 (9)
C1—N3—C2—C7	176.3 (2)	C17—C16—C15—C14	0.4 (8)
C1—N3—C2—C3	−2.3 (5)	C15—C14—C19—C18	0.7 (8)
C1—C8—C9—C10	−179.1 (3)	C8—C9—C10—C11	−1.2 (5)
C1—C8—C13—C12	−179.9 (3)	C9—C8—C13—C12	0.6 (5)
C2—N3—C1—N2	0.8 (5)	C9—C10—C11—C12	0.9 (5)
C2—N3—C1—C8	−179.0 (3)	C10—C11—C12—C13	0.2 (5)
C2—C7—C6—C5	−0.8 (6)	C11—C12—C13—C8	−0.9 (6)
C7—C2—C3—N1	−177.7 (3)	C13—C8—C9—C10	0.5 (5)
C7—C2—C3—C4	−0.1 (5)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20037_0m_2p5349GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.554 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.1831 (9) Å	Cell parameters from 1401 reflections
b = 6.3399 (5) Å	θ = 3.4–24.0°
c = 19.111 (4) Å	µ = 0.09 mm^−1
β = 99.868 (11)°	T = 295 K
V = 1215.6 (3) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	798 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	504 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.055
Detector resolution: 7.9 pixels mm^-1	θmax = 25.8°, θmin = 2.1°
φ and ω scans	h = −12→11
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1003 before and 0.0528 after correction. The Ratio of minimum to maximum transmission is 0.8006. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.597, Tmax = 0.745	l = −8→8
5150 measured reflections

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)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.1006P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
798 reflections	Δρmax = 0.16 e Å^−3
199 parameters	Δρmin = −0.16 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 2.5349 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.10 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.14 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 38 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 4 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4744 (4)	0.6960 (6)	0.6606 (5)	0.038 (4)
N2	0.4430 (3)	0.6863 (6)	0.7269 (5)	0.037 (4)
N3	0.2125 (4)	0.6779 (5)	0.6765 (5)	0.037 (4)
C1	0.3132 (5)	0.6808 (6)	0.7302 (6)	0.032 (4)
C2	0.2447 (5)	0.6770 (6)	0.6099 (6)	0.035 (5)
C7	0.1466 (5)	0.6618 (6)	0.5499 (6)	0.036 (5)
H7	0.057756	0.654723	0.555574	0.044*
C6	0.1766 (5)	0.6568 (6)	0.4823 (6)	0.039 (5)
H6	0.109034	0.646253	0.442974	0.047*
C5	0.3095 (5)	0.6679 (5)	0.4736 (5)	0.041 (5)
H5	0.330786	0.664109	0.428216	0.049*
C4	0.4092 (5)	0.6843 (7)	0.5316 (6)	0.040 (5)
H4	0.497608	0.691289	0.525161	0.047*
C3	0.3795 (5)	0.6904 (6)	0.5993 (5)	0.036 (5)
C14	0.6150 (4)	0.6984 (5)	0.6598 (5)	0.031 (5)
C19	0.6692 (4)	0.8524 (5)	0.6226 (5)	0.038 (6)
H19	0.615032	0.954491	0.597294	0.045*
C18	0.8043 (4)	0.8529 (6)	0.6233 (6)	0.056 (7)
H18	0.841877	0.957793	0.599081	0.067*
C17	0.8837 (4)	0.7023 (7)	0.6591 (6)	0.066 (6)
H17	0.974760	0.702552	0.658270	0.080*
C16	0.8295 (4)	0.5495 (7)	0.6964 (6)	0.062 (7)
H16	0.884319	0.446018	0.720423	0.074*
C15	0.6939 (4)	0.5475 (5)	0.6986 (5)	0.037 (5)
H15	0.657443	0.447753	0.725326	0.044*
C8	0.2810 (5)	0.6785 (6)	0.8032 (6)	0.033 (4)
C9	0.1478 (4)	0.6977 (6)	0.8105 (6)	0.042 (5)
H9	0.080806	0.708746	0.770941	0.051*
C10	0.1183 (6)	0.6999 (6)	0.8787 (5)	0.044 (5)
H10	0.030096	0.715585	0.884635	0.053*
C11	0.2149 (5)	0.6798 (5)	0.9376 (6)	0.047 (5)
H11	0.191802	0.680658	0.982573	0.056*
C12	0.3476 (5)	0.6581 (7)	0.9302 (6)	0.045 (5)
H12	0.414091	0.642019	0.969749	0.054*
C13	0.3781 (5)	0.6611 (7)	0.8627 (6)	0.039 (5)
H13	0.466891	0.651063	0.857168	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.020 (2)	0.0314 (17)	0.066 (14)	−0.0006 (17)	0.017 (4)	−0.007 (4)
N2	0.018 (2)	0.0326 (17)	0.063 (14)	0.0017 (14)	0.011 (4)	−0.003 (4)
N3	0.019 (2)	0.0265 (16)	0.067 (14)	0.0029 (16)	0.010 (4)	−0.002 (4)
C1	0.017 (3)	0.0180 (17)	0.065 (13)	0.0002 (16)	0.014 (4)	0.000 (4)
C2	0.018 (3)	0.0209 (18)	0.065 (14)	0.0025 (18)	0.007 (4)	−0.003 (5)
C7	0.016 (3)	0.0300 (19)	0.063 (14)	0.0042 (18)	0.005 (5)	0.007 (4)
C6	0.028 (3)	0.0291 (19)	0.062 (15)	0.0008 (17)	0.011 (5)	−0.001 (5)
C5	0.031 (3)	0.0286 (19)	0.065 (15)	−0.0002 (18)	0.014 (5)	0.003 (4)
C4	0.024 (3)	0.031 (2)	0.067 (14)	−0.0027 (19)	0.017 (5)	−0.006 (5)
C3	0.023 (3)	0.0217 (18)	0.064 (14)	0.0021 (19)	0.010 (4)	−0.004 (5)
C14	0.015 (2)	0.0309 (18)	0.050 (15)	−0.0018 (15)	0.009 (4)	−0.007 (3)
C19	0.022 (2)	0.034 (2)	0.056 (18)	−0.0021 (15)	0.004 (5)	0.002 (3)
C18	0.025 (3)	0.050 (2)	0.10 (2)	−0.0091 (19)	0.017 (5)	0.000 (4)
C17	0.016 (3)	0.073 (3)	0.11 (2)	0.003 (2)	0.020 (5)	0.001 (5)
C16	0.030 (3)	0.061 (3)	0.10 (2)	0.014 (2)	0.014 (6)	0.004 (4)
C15	0.025 (2)	0.041 (2)	0.047 (17)	0.0045 (17)	0.013 (5)	0.004 (4)
C8	0.015 (3)	0.0215 (17)	0.066 (13)	−0.0006 (17)	0.012 (4)	0.005 (5)
C9	0.024 (3)	0.0261 (19)	0.080 (16)	−0.0022 (16)	0.016 (5)	0.004 (4)
C10	0.024 (3)	0.0276 (19)	0.084 (17)	−0.0036 (18)	0.021 (5)	−0.002 (4)
C11	0.035 (3)	0.0256 (19)	0.082 (17)	−0.0057 (18)	0.019 (5)	−0.005 (4)
C12	0.037 (3)	0.031 (2)	0.068 (15)	−0.0010 (19)	0.014 (5)	−0.001 (5)
C13	0.020 (3)	0.030 (2)	0.069 (14)	0.0000 (19)	0.008 (5)	0.002 (4)

Geometric parameters (Å, º)

N1—N2	1.360 (9)	C19—C18	1.374 (5)
N1—C3	1.386 (8)	C18—H18	0.9300
N1—C14	1.435 (5)	C18—C17	1.357 (7)
N2—C1	1.334 (6)	C17—H17	0.9300
N3—C1	1.321 (8)	C17—C16	1.373 (7)
N3—C2	1.367 (8)	C16—H16	0.9300
C1—C8	1.487 (8)	C16—C15	1.389 (5)
C2—C7	1.389 (8)	C15—H15	0.9300
C2—C3	1.424 (7)	C8—C9	1.393 (6)
C7—H7	0.9300	C8—C13	1.377 (8)
C7—C6	1.379 (9)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.387 (9)
C6—C5	1.393 (6)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.367 (8)
C5—C4	1.373 (8)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.389 (6)
C4—C3	1.379 (9)	C12—H12	0.9300
C14—C19	1.377 (7)	C12—C13	1.377 (9)
C14—C15	1.381 (7)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	123.1 (5)	C18—C19—H19	120.5
N2—N1—C14	113.9 (7)	C19—C18—H18	119.6
C3—N1—C14	122.9 (7)	C17—C18—C19	120.9 (5)
C1—N2—N1	116.0 (7)	C17—C18—H18	119.6
C1—N3—C2	116.4 (5)	C18—C17—H17	120.0
N2—C1—C8	115.1 (7)	C18—C17—C16	120.0 (4)
N3—C1—N2	127.4 (8)	C16—C17—H17	120.0
N3—C1—C8	117.5 (5)	C17—C16—H16	119.6
N3—C2—C7	121.0 (5)	C17—C16—C15	120.8 (5)
N3—C2—C3	121.5 (7)	C15—C16—H16	119.6
C7—C2—C3	117.5 (7)	C14—C15—C16	117.9 (5)
C2—C7—H7	118.9	C14—C15—H15	121.1
C6—C7—C2	122.1 (5)	C16—C15—H15	121.1
C6—C7—H7	118.9	C9—C8—C1	117.9 (7)
C7—C6—H6	120.4	C13—C8—C1	122.2 (5)
C7—C6—C5	119.1 (8)	C13—C8—C9	119.9 (8)
C5—C6—H6	120.4	C8—C9—H9	121.1
C6—C5—H5	119.8	C10—C9—C8	117.8 (8)
C4—C5—C6	120.5 (8)	C10—C9—H9	121.1
C4—C5—H5	119.8	C9—C10—H10	119.0
C5—C4—H4	119.7	C11—C10—C9	122.1 (5)
C5—C4—C3	120.6 (5)	C11—C10—H10	119.0
C3—C4—H4	119.7	C10—C11—H11	120.0
N1—C3—C2	115.5 (7)	C10—C11—C12	120.1 (8)
C4—C3—N1	124.1 (5)	C12—C11—H11	120.0
C4—C3—C2	120.2 (7)	C11—C12—H12	120.9
C19—C14—N1	120.1 (4)	C13—C12—C11	118.2 (8)
C19—C14—C15	121.4 (3)	C13—C12—H12	120.9
C15—C14—N1	118.5 (5)	C8—C13—H13	119.0
C14—C19—H19	120.5	C12—C13—C8	121.9 (6)
C18—C19—C14	119.0 (5)	C12—C13—H13	119.0
N1—N2—C1—N3	2.0 (7)	C7—C6—C5—C4	−0.2 (6)
N1—N2—C1—C8	−177.8 (4)	C6—C5—C4—C3	−0.1 (7)
N1—C14—C19—C18	179.1 (8)	C5—C4—C3—N1	176.6 (3)
N1—C14—C15—C16	179.0 (8)	C5—C4—C3—C2	0.8 (7)
N2—N1—C3—C2	1.0 (7)	C3—N1—N2—C1	−3.0 (7)
N2—N1—C3—C4	−175.0 (4)	C3—N1—C14—C19	55.8 (8)
N2—N1—C14—C19	−128.1 (7)	C3—N1—C14—C15	−126.1 (7)
N2—N1—C14—C15	50.0 (8)	C3—C2—C7—C6	0.8 (7)
N2—C1—C8—C9	172.6 (3)	C14—N1—N2—C1	−179.1 (3)
N2—C1—C8—C13	−6.5 (7)	C14—N1—C3—C2	176.7 (3)
N3—C1—C8—C9	−7.2 (6)	C14—N1—C3—C4	0.7 (8)
N3—C1—C8—C13	173.7 (3)	C14—C19—C18—C17	1.2 (12)
N3—C2—C7—C6	−178.8 (4)	C19—C14—C15—C16	−2.9 (11)
N3—C2—C3—N1	2.4 (6)	C19—C18—C17—C16	−1.5 (13)
N3—C2—C3—C4	178.5 (5)	C18—C17—C16—C15	−0.5 (13)
C1—N3—C2—C7	176.3 (3)	C17—C16—C15—C14	2.6 (12)
C1—N3—C2—C3	−3.3 (7)	C15—C14—C19—C18	1.1 (12)
C1—C8—C9—C10	−178.7 (4)	C8—C9—C10—C11	−1.3 (7)
C1—C8—C13—C12	−179.7 (4)	C9—C8—C13—C12	1.2 (7)
C2—N3—C1—N2	1.1 (7)	C9—C10—C11—C12	0.6 (7)
C2—N3—C1—C8	−179.1 (3)	C10—C11—C12—C13	1.1 (6)
C2—C7—C6—C5	−0.1 (7)	C11—C12—C13—C8	−2.0 (8)
C7—C2—C3—N1	−177.3 (4)	C13—C8—C9—C10	0.4 (6)
C7—C2—C3—C4	−1.2 (6)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20051_0m_2p5349GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.554 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.1864 (8) Å	Cell parameters from 1975 reflections
b = 6.3323 (5) Å	θ = 3.4–25.1°
c = 19.118 (3) Å	µ = 0.09 mm^−1
β = 99.822 (9)°	T = 276 K
V = 1215.1 (3) Å^3	Block, clear dark brown
Z = 4	0.18 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	865 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	558 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.050
Detector resolution: 7.9 pixels mm^-1	θmax = 26.3°, θmin = 2.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1563 before and 0.0780 after correction. The Ratio of minimum to maximum transmission is 0.8154. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.608, Tmax = 0.745	l = −8→8
6204 measured reflections

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)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0716P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
865 reflections	Δρmax = 0.14 e Å^−3
199 parameters	Δρmin = −0.12 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 2.5349 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.14 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 49 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 2 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4739 (3)	0.6963 (4)	0.6606 (4)	0.029 (3)
N2	0.4428 (2)	0.6863 (4)	0.7271 (3)	0.029 (3)
N3	0.2118 (3)	0.6774 (4)	0.6756 (4)	0.028 (3)
C1	0.3118 (3)	0.6799 (4)	0.7301 (4)	0.022 (3)
C2	0.2449 (3)	0.6772 (4)	0.6089 (4)	0.024 (3)
C7	0.1460 (3)	0.6615 (4)	0.5498 (4)	0.027 (3)
H7	0.057247	0.654255	0.555526	0.032*
C6	0.1768 (3)	0.6564 (4)	0.4833 (4)	0.030 (3)
H6	0.108947	0.645142	0.444219	0.037*
C5	0.3091 (3)	0.6680 (4)	0.4729 (4)	0.032 (3)
H5	0.328948	0.663824	0.427254	0.039*
C4	0.4095 (3)	0.6855 (5)	0.5303 (4)	0.030 (3)
H4	0.497627	0.694245	0.523577	0.036*
C3	0.3792 (3)	0.6900 (4)	0.5982 (4)	0.027 (3)
C14	0.6150 (2)	0.6987 (4)	0.6599 (3)	0.024 (3)
C19	0.6690 (2)	0.8524 (4)	0.6224 (4)	0.029 (4)
H19	0.614744	0.954917	0.597465	0.035*
C18	0.8045 (3)	0.8528 (4)	0.6223 (4)	0.041 (4)
H18	0.841845	0.955457	0.596973	0.049*
C17	0.8837 (3)	0.7028 (5)	0.6594 (4)	0.047 (4)
H17	0.975050	0.704387	0.659427	0.056*
C16	0.8295 (3)	0.5488 (5)	0.6967 (4)	0.040 (4)
H16	0.884073	0.446280	0.721509	0.048*
C15	0.6934 (2)	0.5467 (4)	0.6974 (3)	0.032 (4)
H15	0.656014	0.444215	0.722859	0.038*
C8	0.2808 (3)	0.6784 (4)	0.8030 (4)	0.024 (3)
C9	0.1484 (3)	0.6974 (4)	0.8119 (4)	0.034 (3)
H9	0.081017	0.708815	0.772541	0.041*
C10	0.1182 (3)	0.6992 (5)	0.8793 (4)	0.037 (4)
H10	0.029893	0.714255	0.885100	0.044*
C11	0.2158 (3)	0.6793 (4)	0.9384 (4)	0.040 (4)
H11	0.193389	0.679826	0.983571	0.047*
C12	0.3476 (3)	0.6585 (5)	0.9299 (5)	0.031 (3)
H12	0.414443	0.643532	0.969301	0.037*
C13	0.3787 (4)	0.6603 (5)	0.8626 (4)	0.029 (3)
H13	0.467391	0.649057	0.856991	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0205 (15)	0.0346 (14)	0.036 (10)	−0.0001 (11)	0.017 (3)	−0.006 (2)
N2	0.0206 (15)	0.0342 (14)	0.036 (9)	−0.0007 (10)	0.013 (3)	−0.005 (3)
N3	0.0206 (16)	0.0288 (14)	0.034 (9)	0.0018 (10)	0.006 (3)	−0.001 (2)
C1	0.0193 (16)	0.0166 (15)	0.030 (9)	0.0003 (11)	0.008 (3)	−0.003 (3)
C2	0.0223 (19)	0.0215 (15)	0.030 (10)	0.0019 (12)	0.009 (3)	−0.003 (3)
C7	0.0174 (16)	0.0328 (17)	0.030 (10)	0.0017 (12)	0.005 (3)	0.002 (3)
C6	0.031 (2)	0.0320 (17)	0.030 (11)	0.0006 (12)	0.011 (3)	−0.002 (3)
C5	0.0295 (17)	0.0342 (17)	0.036 (11)	0.0004 (12)	0.012 (3)	0.000 (2)
C4	0.0244 (18)	0.0339 (17)	0.036 (10)	−0.0013 (13)	0.016 (3)	0.000 (3)
C3	0.0211 (18)	0.0227 (15)	0.037 (10)	−0.0003 (12)	0.007 (3)	−0.005 (3)
C14	0.0147 (13)	0.0329 (16)	0.025 (11)	−0.0002 (10)	0.006 (2)	−0.005 (2)
C19	0.0240 (14)	0.0346 (18)	0.029 (12)	−0.0039 (10)	0.004 (3)	−0.004 (2)
C18	0.0238 (15)	0.055 (2)	0.046 (14)	−0.0110 (12)	0.011 (3)	−0.002 (3)
C17	0.0188 (15)	0.073 (3)	0.051 (13)	0.0008 (14)	0.015 (3)	0.001 (3)
C16	0.0308 (16)	0.062 (2)	0.025 (14)	0.0156 (14)	0.002 (3)	0.006 (3)
C15	0.0270 (14)	0.0414 (19)	0.029 (12)	0.0005 (12)	0.011 (3)	0.001 (3)
C8	0.0224 (18)	0.0220 (15)	0.031 (9)	0.0004 (12)	0.012 (3)	−0.004 (3)
C9	0.0233 (18)	0.0282 (16)	0.054 (11)	−0.0031 (11)	0.015 (3)	0.001 (3)
C10	0.0242 (17)	0.0316 (17)	0.059 (11)	−0.0033 (13)	0.018 (3)	−0.003 (3)
C11	0.0400 (19)	0.0288 (17)	0.055 (12)	−0.0047 (12)	0.022 (3)	−0.003 (3)
C12	0.0322 (19)	0.0328 (18)	0.028 (10)	−0.0035 (12)	0.002 (3)	−0.006 (3)
C13	0.0273 (18)	0.0292 (17)	0.034 (10)	0.0008 (13)	0.012 (3)	0.000 (3)

Geometric parameters (Å, º)

N1—N2	1.362 (8)	C19—C18	1.381 (3)
N1—C3	1.401 (7)	C18—H18	0.9300
N1—C14	1.440 (4)	C18—C17	1.364 (5)
N2—C1	1.347 (4)	C17—H17	0.9300
N3—C1	1.327 (6)	C17—C16	1.379 (5)
N3—C2	1.375 (7)	C16—H16	0.9300
C1—C8	1.480 (7)	C16—C15	1.389 (3)
C2—C7	1.383 (7)	C15—H15	0.9300
C2—C3	1.420 (5)	C8—C9	1.393 (5)
C7—H7	0.9300	C8—C13	1.385 (7)
C7—C6	1.360 (8)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.375 (8)
C6—C5	1.397 (5)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.377 (7)
C5—C4	1.370 (7)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.387 (4)
C4—C3	1.386 (8)	C12—H12	0.9300
C14—C19	1.377 (5)	C12—C13	1.377 (8)
C14—C15	1.373 (5)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	123.9 (3)	C18—C19—H19	120.3
N2—N1—C14	113.6 (5)	C19—C18—H18	120.0
C3—N1—C14	122.3 (5)	C17—C18—C19	120.1 (4)
C1—N2—N1	115.6 (5)	C17—C18—H18	120.0
C1—N3—C2	116.9 (4)	C18—C17—H17	119.7
N2—C1—C8	114.4 (5)	C18—C17—C16	120.5 (3)
N3—C1—N2	126.9 (6)	C16—C17—H17	119.7
N3—C1—C8	118.7 (4)	C17—C16—H16	120.0
N3—C2—C7	119.9 (4)	C17—C16—C15	120.0 (3)
N3—C2—C3	121.9 (6)	C15—C16—H16	120.0
C7—C2—C3	118.2 (6)	C14—C15—C16	118.7 (4)
C2—C7—H7	119.6	C14—C15—H15	120.6
C6—C7—C2	120.8 (4)	C16—C15—H15	120.6
C6—C7—H7	119.6	C9—C8—C1	118.7 (5)
C7—C6—H6	119.6	C13—C8—C1	122.4 (4)
C7—C6—C5	120.9 (6)	C13—C8—C9	118.9 (6)
C5—C6—H6	119.6	C8—C9—H9	120.3
C6—C5—H5	120.1	C10—C9—C8	119.4 (6)
C4—C5—C6	119.8 (6)	C10—C9—H9	120.3
C4—C5—H5	120.1	C9—C10—H10	119.2
C5—C4—H4	120.1	C9—C10—C11	121.5 (4)
C5—C4—C3	119.8 (4)	C11—C10—H10	119.2
C3—C4—H4	120.1	C10—C11—H11	120.3
N1—C3—C2	114.8 (6)	C10—C11—C12	119.4 (6)
C4—C3—N1	124.7 (4)	C12—C11—H11	120.3
C4—C3—C2	120.5 (5)	C11—C12—H12	120.3
C19—C14—N1	120.1 (3)	C13—C12—C11	119.4 (6)
C15—C14—N1	118.6 (3)	C13—C12—H12	120.3
C15—C14—C19	121.3 (2)	C8—C13—H13	119.3
C14—C19—H19	120.3	C12—C13—C8	121.4 (4)
C14—C19—C18	119.4 (3)	C12—C13—H13	119.3
N1—N2—C1—N3	1.7 (4)	C7—C6—C5—C4	−0.3 (4)
N1—N2—C1—C8	−177.5 (2)	C6—C5—C4—C3	0.5 (4)
N1—C14—C19—C18	179.9 (5)	C5—C4—C3—N1	176.5 (2)
N1—C14—C15—C16	180.0 (5)	C5—C4—C3—C2	−0.2 (5)
N2—N1—C3—C2	1.5 (4)	C3—N1—N2—C1	−3.1 (5)
N2—N1—C3—C4	−175.4 (3)	C3—N1—C14—C19	55.7 (5)
N2—N1—C14—C19	−128.5 (5)	C3—N1—C14—C15	−124.8 (5)
N2—N1—C14—C15	51.0 (5)	C3—C2—C7—C6	0.6 (5)
N2—C1—C8—C9	172.4 (2)	C14—N1—N2—C1	−178.88 (19)
N2—C1—C8—C13	−7.1 (5)	C14—N1—C3—C2	176.8 (2)
N3—C1—C8—C9	−6.8 (4)	C14—N1—C3—C4	0.0 (5)
N3—C1—C8—C13	173.6 (2)	C14—C19—C18—C17	−0.4 (8)
N3—C2—C7—C6	−178.6 (3)	C19—C14—C15—C16	−0.5 (8)
N3—C2—C3—N1	1.8 (4)	C19—C18—C17—C16	0.5 (8)
N3—C2—C3—C4	178.8 (3)	C18—C17—C16—C15	−0.6 (8)
C1—N3—C2—C7	176.0 (2)	C17—C16—C15—C14	0.6 (8)
C1—N3—C2—C3	−3.2 (4)	C15—C14—C19—C18	0.4 (8)
C1—C8—C9—C10	−179.1 (3)	C8—C9—C10—C11	−1.0 (5)
C1—C8—C13—C12	−179.8 (3)	C9—C8—C13—C12	0.7 (5)
C2—N3—C1—N2	1.4 (4)	C9—C10—C11—C12	0.5 (4)
C2—N3—C1—C8	−179.5 (2)	C10—C11—C12—C13	0.6 (4)
C2—C7—C6—C5	−0.3 (5)	C11—C12—C13—C8	−1.2 (5)
C7—C2—C3—N1	−177.3 (3)	C13—C8—C9—C10	0.5 (4)
C7—C2—C3—C4	−0.4 (4)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20039_0m_3p4218GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.605 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.1302 (4) Å	Cell parameters from 2011 reflections
b = 6.2215 (3) Å	θ = 3.5–25.9°
c = 18.9550 (18) Å	µ = 0.10 mm^−1
β = 99.899 (5)°	T = 295 K
V = 1176.85 (13) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	805 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	558 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.035
Detector resolution: 7.9 pixels mm^-1	θmax = 26.3°, θmin = 2.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0569 before and 0.0430 after correction. The Ratio of minimum to maximum transmission is 0.8822. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.658, Tmax = 0.745	l = −8→8
5411 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0665P)^2 + 0.0073P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
805 reflections	Δρmax = 0.10 e Å^−3
199 parameters	Δρmin = −0.11 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 3.4218 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.16 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.07 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.19 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.11 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.15 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 53 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 3 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4740 (3)	0.6901 (4)	0.6613 (4)	0.031 (3)
N2	0.4433 (2)	0.6776 (4)	0.7285 (4)	0.032 (3)
N3	0.2112 (3)	0.6706 (4)	0.6774 (4)	0.031 (4)
C1	0.3113 (3)	0.6722 (4)	0.7312 (4)	0.027 (4)
C2	0.2436 (3)	0.6725 (5)	0.6100 (4)	0.030 (4)
C7	0.1444 (3)	0.6591 (4)	0.5499 (4)	0.029 (4)
H7	0.055091	0.651835	0.555559	0.035*
C6	0.1750 (3)	0.6563 (4)	0.4826 (4)	0.032 (4)
H6	0.106866	0.645671	0.443033	0.039*
C5	0.3084 (3)	0.6694 (3)	0.4729 (4)	0.033 (4)
H5	0.328989	0.667662	0.426908	0.039*
C4	0.4093 (3)	0.6850 (5)	0.5312 (4)	0.032 (4)
H4	0.498085	0.694484	0.524809	0.039*
C3	0.3787 (3)	0.6865 (5)	0.5994 (4)	0.029 (4)
C14	0.6152 (2)	0.6930 (3)	0.6609 (3)	0.018 (3)
C19	0.6694 (2)	0.8515 (3)	0.6239 (4)	0.026 (4)
H19	0.614485	0.956137	0.599012	0.032*
C18	0.8058 (2)	0.8540 (4)	0.6241 (4)	0.043 (5)
H18	0.843087	0.962055	0.599882	0.051*
C17	0.8857 (2)	0.6989 (4)	0.6595 (3)	0.038 (4)
H17	0.977311	0.700278	0.659063	0.045*
C16	0.8311 (2)	0.5402 (4)	0.6960 (4)	0.033 (4)
H16	0.886268	0.433634	0.719514	0.039*
C15	0.6952 (2)	0.5369 (4)	0.6982 (3)	0.030 (4)
H15	0.658787	0.432187	0.724200	0.036*
C8	0.2804 (3)	0.6710 (4)	0.8049 (4)	0.029 (4)
C9	0.1464 (3)	0.6910 (4)	0.8128 (4)	0.033 (4)
H9	0.078925	0.700642	0.772871	0.040*
C10	0.1165 (3)	0.6961 (5)	0.8810 (4)	0.035 (4)
H10	0.027820	0.712569	0.886891	0.042*
C11	0.2143 (3)	0.6775 (3)	0.9402 (4)	0.039 (4)
H11	0.191310	0.679733	0.985630	0.046*
C12	0.3474 (3)	0.6554 (5)	0.9329 (5)	0.038 (4)
H12	0.414183	0.641357	0.972897	0.045*
C13	0.3786 (3)	0.6547 (5)	0.8648 (4)	0.033 (4)
H13	0.467699	0.642918	0.859165	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0175 (14)	0.0273 (11)	0.052 (11)	−0.0002 (9)	0.014 (3)	−0.003 (3)
N2	0.0175 (14)	0.0259 (11)	0.054 (11)	−0.0008 (9)	0.010 (3)	−0.004 (3)
N3	0.0159 (15)	0.0224 (11)	0.053 (11)	0.0001 (10)	0.001 (3)	−0.004 (3)
C1	0.0132 (15)	0.0163 (12)	0.051 (11)	0.0010 (10)	0.005 (3)	0.001 (3)
C2	0.0206 (18)	0.0160 (12)	0.054 (11)	0.0028 (11)	0.008 (3)	0.001 (3)
C7	0.0154 (15)	0.0230 (13)	0.050 (12)	0.0015 (11)	0.004 (3)	0.000 (3)
C6	0.0247 (18)	0.0238 (13)	0.049 (12)	0.0007 (11)	0.009 (3)	0.000 (3)
C5	0.0259 (15)	0.0259 (13)	0.047 (12)	−0.0010 (10)	0.008 (3)	−0.003 (2)
C4	0.0198 (17)	0.0259 (13)	0.053 (11)	−0.0029 (12)	0.010 (3)	−0.001 (3)
C3	0.0157 (16)	0.0194 (12)	0.052 (11)	−0.0004 (11)	0.003 (3)	−0.003 (3)
C14	0.0156 (12)	0.0288 (13)	0.010 (11)	−0.0004 (9)	0.003 (2)	−0.006 (2)
C19	0.0230 (13)	0.0291 (13)	0.027 (13)	−0.0013 (9)	0.005 (3)	−0.001 (2)
C18	0.0216 (14)	0.0486 (16)	0.059 (15)	−0.0093 (11)	0.009 (3)	0.001 (2)
C17	0.0141 (13)	0.0668 (19)	0.032 (14)	0.0006 (12)	0.001 (3)	−0.003 (3)
C16	0.0271 (14)	0.0526 (17)	0.014 (14)	0.0152 (12)	−0.007 (3)	−0.002 (3)
C15	0.0238 (13)	0.0361 (14)	0.031 (12)	0.0035 (10)	0.008 (3)	0.001 (2)
C8	0.0194 (17)	0.0160 (12)	0.052 (11)	−0.0023 (11)	0.011 (3)	−0.004 (3)
C9	0.0197 (17)	0.0210 (12)	0.060 (12)	−0.0022 (10)	0.008 (3)	0.006 (3)
C10	0.0227 (16)	0.0245 (13)	0.061 (13)	−0.0044 (12)	0.013 (3)	0.000 (3)
C11	0.0359 (17)	0.0200 (12)	0.062 (13)	−0.0025 (10)	0.014 (3)	0.005 (2)
C12	0.0293 (19)	0.0246 (13)	0.058 (12)	−0.0021 (11)	0.005 (4)	−0.003 (3)
C13	0.0166 (15)	0.0246 (13)	0.057 (12)	−0.0009 (12)	0.002 (3)	−0.003 (3)

Geometric parameters (Å, º)

N1—N2	1.365 (8)	C19—C18	1.381 (3)
N1—C3	1.386 (7)	C18—H18	0.9300
N1—C14	1.432 (3)	C18—C17	1.360 (5)
N2—C1	1.347 (4)	C17—H17	0.9300
N3—C1	1.309 (7)	C17—C16	1.375 (5)
N3—C2	1.372 (8)	C16—H16	0.9300
C1—C8	1.483 (8)	C16—C15	1.385 (3)
C2—C7	1.387 (7)	C15—H15	0.9300
C2—C3	1.420 (5)	C8—C9	1.397 (5)
C7—H7	0.9300	C8—C13	1.377 (7)
C7—C6	1.364 (8)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.378 (8)
C6—C5	1.398 (4)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.368 (7)
C5—C4	1.374 (7)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.386 (4)
C4—C3	1.379 (8)	C12—H12	0.9300
C14—C19	1.377 (5)	C12—C13	1.381 (8)
C14—C15	1.380 (5)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	123.5 (4)	C18—C19—H19	120.2
N2—N1—C14	113.2 (5)	C19—C18—H18	119.9
C3—N1—C14	123.1 (6)	C17—C18—C19	120.2 (4)
C1—N2—N1	115.1 (6)	C17—C18—H18	119.9
C1—N3—C2	116.6 (4)	C18—C17—H17	120.0
N2—C1—C8	114.0 (5)	C18—C17—C16	120.1 (2)
N3—C1—N2	127.7 (7)	C16—C17—H17	120.0
N3—C1—C8	118.2 (4)	C17—C16—H16	119.5
N3—C2—C7	120.6 (4)	C17—C16—C15	120.9 (3)
N3—C2—C3	121.5 (6)	C15—C16—H16	119.5
C7—C2—C3	117.8 (6)	C14—C15—C16	118.2 (4)
C2—C7—H7	119.3	C14—C15—H15	120.9
C6—C7—C2	121.4 (4)	C16—C15—H15	120.9
C6—C7—H7	119.3	C9—C8—C1	117.8 (5)
C7—C6—H6	119.9	C13—C8—C1	122.5 (4)
C7—C6—C5	120.2 (6)	C13—C8—C9	119.7 (7)
C5—C6—H6	119.9	C8—C9—H9	120.8
C6—C5—H5	120.0	C10—C9—C8	118.4 (6)
C4—C5—C6	120.0 (6)	C10—C9—H9	120.8
C4—C5—H5	120.0	C9—C10—H10	119.2
C5—C4—H4	120.0	C11—C10—C9	121.5 (4)
C5—C4—C3	119.9 (3)	C11—C10—H10	119.2
C3—C4—H4	120.0	C10—C11—H11	119.8
N1—C3—C2	115.4 (6)	C10—C11—C12	120.4 (6)
C4—C3—N1	123.8 (4)	C12—C11—H11	119.8
C4—C3—C2	120.7 (5)	C11—C12—H12	120.8
C19—C14—N1	119.8 (3)	C13—C12—C11	118.5 (6)
C19—C14—C15	121.0 (2)	C13—C12—H12	120.8
C15—C14—N1	119.1 (3)	C8—C13—C12	121.4 (4)
C14—C19—H19	120.2	C8—C13—H13	119.3
C14—C19—C18	119.5 (3)	C12—C13—H13	119.3
N1—N2—C1—N3	2.3 (4)	C7—C6—C5—C4	0.1 (4)
N1—N2—C1—C8	−176.8 (3)	C6—C5—C4—C3	0.3 (5)
N1—C14—C19—C18	179.6 (5)	C5—C4—C3—N1	176.4 (2)
N1—C14—C15—C16	178.8 (5)	C5—C4—C3—C2	−0.1 (6)
N2—N1—C3—C2	1.1 (4)	C3—N1—N2—C1	−3.2 (5)
N2—N1—C3—C4	−175.6 (3)	C3—N1—C14—C19	55.6 (5)
N2—N1—C14—C19	−128.3 (5)	C3—N1—C14—C15	−125.0 (5)
N2—N1—C14—C15	51.2 (5)	C3—C2—C7—C6	0.9 (5)
N2—C1—C8—C9	172.6 (2)	C14—N1—N2—C1	−179.31 (18)
N2—C1—C8—C13	−6.3 (5)	C14—N1—C3—C2	176.8 (2)
N3—C1—C8—C9	−6.6 (4)	C14—N1—C3—C4	0.1 (5)
N3—C1—C8—C13	174.5 (2)	C14—C19—C18—C17	1.1 (8)
N3—C2—C7—C6	−178.6 (3)	C19—C14—C15—C16	−1.7 (8)
N3—C2—C3—N1	2.2 (5)	C19—C18—C17—C16	−0.7 (8)
N3—C2—C3—C4	179.0 (3)	C18—C17—C16—C15	−0.9 (8)
C1—N3—C2—C7	176.4 (2)	C17—C16—C15—C14	2.1 (8)
C1—N3—C2—C3	−3.0 (5)	C15—C14—C19—C18	0.2 (8)
C1—C8—C9—C10	−178.2 (3)	C8—C9—C10—C11	−1.4 (5)
C1—C8—C13—C12	179.6 (3)	C9—C8—C13—C12	0.7 (5)
C2—N3—C1—N2	0.7 (5)	C9—C10—C11—C12	0.8 (4)
C2—N3—C1—C8	179.8 (3)	C10—C11—C12—C13	0.6 (4)
C2—C7—C6—C5	−0.7 (5)	C11—C12—C13—C8	−1.3 (5)
C7—C2—C3—N1	−177.3 (2)	C13—C8—C9—C10	0.7 (4)
C7—C2—C3—C4	−0.5 (5)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (sp20042_0m_4p0054GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.638 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.0953 (4) Å	Cell parameters from 1769 reflections
b = 6.1527 (3) Å	θ = 3.5–25.5°
c = 18.8502 (18) Å	µ = 0.10 mm^−1
β = 99.934 (5)°	T = 271 K
V = 1153.29 (13) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	772 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	518 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.043
Detector resolution: 7.9 pixels mm^-1	θmax = 26.4°, θmin = 2.2°
ω and φ scans	h = −11→11
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0612 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.9141. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.681, Tmax = 0.745	l = −8→8
6509 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 0.2042P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
772 reflections	Δρmax = 0.11 e Å^−3
199 parameters	Δρmin = −0.11 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 4.0054 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.13 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C12 3.19 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.02 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.16 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.07 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.11 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 52 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 3 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4745 (3)	0.6858 (4)	0.6626 (4)	0.030 (4)
N2	0.4435 (3)	0.6713 (4)	0.7299 (4)	0.030 (4)
N3	0.2099 (3)	0.6652 (4)	0.6780 (5)	0.028 (4)
C1	0.3116 (3)	0.6656 (4)	0.7323 (5)	0.024 (4)
C2	0.2427 (4)	0.6687 (5)	0.6107 (5)	0.025 (4)
C7	0.1437 (4)	0.6565 (5)	0.5498 (5)	0.029 (4)
H7	0.054182	0.648274	0.555454	0.035*
C6	0.1735 (3)	0.6563 (5)	0.4819 (5)	0.030 (4)
H6	0.104906	0.646806	0.442158	0.036*
C5	0.3082 (3)	0.6705 (4)	0.4721 (4)	0.032 (4)
H5	0.329117	0.669836	0.425899	0.038*
C4	0.4092 (4)	0.6854 (5)	0.5314 (5)	0.030 (4)
H4	0.498270	0.696908	0.525152	0.036*
C3	0.3785 (3)	0.6833 (5)	0.6002 (4)	0.027 (4)
C14	0.6159 (2)	0.6893 (4)	0.6619 (3)	0.018 (4)
C19	0.6696 (3)	0.8518 (4)	0.6259 (4)	0.021 (4)
H19	0.614260	0.959046	0.601853	0.025*
C18	0.8058 (3)	0.8553 (5)	0.6254 (4)	0.043 (5)
H18	0.842627	0.965103	0.601032	0.052*
C17	0.8869 (3)	0.6982 (5)	0.6607 (4)	0.033 (4)
H17	0.979069	0.701891	0.660819	0.040*
C16	0.8326 (3)	0.5343 (5)	0.6962 (4)	0.039 (5)
H16	0.887926	0.425940	0.719492	0.046*
C15	0.6958 (2)	0.5299 (5)	0.6973 (4)	0.032 (4)
H15	0.658899	0.420348	0.721777	0.038*
C8	0.2798 (3)	0.6664 (4)	0.8061 (5)	0.023 (4)
C9	0.1453 (3)	0.6855 (5)	0.8142 (4)	0.033 (4)
H9	0.077025	0.692110	0.774257	0.040*
C10	0.1162 (4)	0.6943 (5)	0.8834 (4)	0.035 (4)
H10	0.027378	0.713032	0.889449	0.042*
C11	0.2141 (3)	0.6761 (4)	0.9430 (5)	0.036 (4)
H11	0.191675	0.679110	0.988778	0.044*
C12	0.3469 (3)	0.6533 (5)	0.9346 (5)	0.029 (4)
H12	0.414330	0.640203	0.974729	0.035*
C13	0.3783 (4)	0.6503 (5)	0.8668 (5)	0.027 (4)
H13	0.467811	0.637045	0.861388	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0183 (16)	0.0282 (13)	0.045 (11)	−0.0003 (11)	0.013 (3)	−0.001 (3)
N2	0.0157 (16)	0.0280 (13)	0.047 (11)	−0.0022 (10)	0.005 (3)	−0.005 (3)
N3	0.0180 (17)	0.0233 (13)	0.043 (11)	0.0000 (12)	0.005 (3)	−0.004 (3)
C1	0.0153 (17)	0.0152 (14)	0.041 (11)	0.0004 (12)	0.007 (3)	−0.001 (3)
C2	0.0172 (19)	0.0151 (14)	0.041 (12)	0.0032 (12)	0.003 (3)	0.005 (4)
C7	0.0179 (18)	0.0227 (16)	0.044 (12)	0.0011 (13)	−0.001 (3)	0.003 (4)
C6	0.026 (2)	0.0233 (16)	0.037 (13)	−0.0002 (13)	−0.002 (4)	0.001 (4)
C5	0.0239 (17)	0.0260 (15)	0.044 (12)	−0.0014 (11)	0.004 (3)	0.000 (3)
C4	0.0182 (18)	0.0255 (15)	0.048 (12)	−0.0011 (13)	0.008 (3)	−0.004 (4)
C3	0.0156 (18)	0.0165 (14)	0.047 (11)	−0.0002 (12)	0.003 (3)	−0.006 (4)
C14	0.0116 (13)	0.0293 (15)	0.012 (12)	0.0000 (11)	0.000 (3)	−0.005 (2)
C19	0.0195 (15)	0.0313 (16)	0.011 (14)	−0.0018 (10)	0.000 (3)	−0.004 (2)
C18	0.0213 (16)	0.0467 (19)	0.062 (17)	−0.0085 (12)	0.006 (4)	0.008 (3)
C17	0.0162 (14)	0.062 (2)	0.022 (14)	−0.0004 (14)	0.006 (3)	−0.008 (3)
C16	0.0250 (16)	0.053 (2)	0.034 (15)	0.0151 (14)	−0.005 (4)	0.003 (3)
C15	0.0243 (15)	0.0370 (17)	0.035 (14)	0.0033 (11)	0.006 (3)	0.009 (3)
C8	0.0142 (18)	0.0164 (14)	0.039 (11)	0.0013 (12)	0.006 (3)	−0.003 (4)
C9	0.0206 (19)	0.0213 (15)	0.057 (13)	−0.0022 (12)	0.005 (3)	0.002 (4)
C10	0.0205 (18)	0.0235 (16)	0.062 (13)	−0.0040 (13)	0.008 (4)	−0.003 (3)
C11	0.0301 (18)	0.0202 (15)	0.060 (14)	−0.0032 (12)	0.012 (3)	−0.001 (3)
C12	0.027 (2)	0.0242 (16)	0.035 (13)	−0.0015 (13)	−0.002 (4)	−0.004 (4)
C13	0.0174 (18)	0.0229 (16)	0.041 (12)	0.0037 (13)	0.006 (3)	−0.006 (3)

Geometric parameters (Å, º)

N1—N2	1.359 (8)	C19—C18	1.377 (3)
N1—C3	1.390 (7)	C18—H18	0.9300
N1—C14	1.430 (4)	C18—C17	1.364 (6)
N2—C1	1.341 (4)	C17—H17	0.9300
N3—C1	1.318 (7)	C17—C16	1.375 (6)
N3—C2	1.367 (8)	C16—H16	0.9300
C1—C8	1.481 (8)	C16—C15	1.385 (3)
C2—C7	1.388 (8)	C15—H15	0.9300
C2—C3	1.421 (5)	C8—C9	1.398 (5)
C7—H7	0.9300	C8—C13	1.384 (8)
C7—C6	1.365 (9)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.386 (8)
C6—C5	1.406 (5)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.367 (8)
C5—C4	1.380 (7)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.384 (4)
C4—C3	1.383 (8)	C12—H12	0.9300
C14—C19	1.372 (5)	C12—C13	1.369 (8)
C14—C15	1.369 (5)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	123.4 (4)	C18—C19—H19	120.2
N2—N1—C14	113.6 (5)	C19—C18—H18	119.9
C3—N1—C14	122.9 (6)	C17—C18—C19	120.2 (4)
C1—N2—N1	115.0 (6)	C17—C18—H18	119.9
C1—N3—C2	116.0 (4)	C18—C17—H17	120.0
N2—C1—C8	114.1 (6)	C18—C17—C16	120.0 (3)
N3—C1—N2	128.3 (7)	C16—C17—H17	120.0
N3—C1—C8	117.6 (4)	C17—C16—H16	119.9
N3—C2—C7	120.8 (4)	C17—C16—C15	120.3 (3)
N3—C2—C3	121.7 (6)	C15—C16—H16	119.9
C7—C2—C3	117.5 (6)	C14—C15—C16	119.0 (4)
C2—C7—H7	118.9	C14—C15—H15	120.5
C6—C7—C2	122.2 (4)	C16—C15—H15	120.5
C6—C7—H7	118.9	C9—C8—C1	118.4 (6)
C7—C6—H6	120.1	C13—C8—C1	122.4 (4)
C7—C6—C5	119.9 (6)	C13—C8—C9	119.2 (7)
C5—C6—H6	120.1	C8—C9—H9	120.8
C6—C5—H5	120.2	C10—C9—C8	118.3 (6)
C4—C5—C6	119.5 (6)	C10—C9—H9	120.8
C4—C5—H5	120.2	C9—C10—H10	119.0
C5—C4—H4	119.8	C11—C10—C9	121.9 (4)
C5—C4—C3	120.4 (4)	C11—C10—H10	119.0
C3—C4—H4	119.8	C10—C11—H11	120.3
N1—C3—C2	115.5 (6)	C10—C11—C12	119.5 (7)
C4—C3—N1	123.9 (4)	C12—C11—H11	120.3
C4—C3—C2	120.5 (6)	C11—C12—H12	120.2
C19—C14—N1	119.8 (3)	C13—C12—C11	119.5 (6)
C15—C14—N1	119.4 (3)	C13—C12—H12	120.2
C15—C14—C19	120.9 (2)	C8—C13—H13	119.3
C14—C19—H19	120.2	C12—C13—C8	121.4 (4)
C14—C19—C18	119.7 (4)	C12—C13—H13	119.3
N1—N2—C1—N3	2.4 (5)	C7—C6—C5—C4	−0.3 (4)
N1—N2—C1—C8	−175.7 (3)	C6—C5—C4—C3	0.9 (5)
N1—C14—C19—C18	179.7 (6)	C5—C4—C3—N1	176.4 (2)
N1—C14—C15—C16	179.9 (5)	C5—C4—C3—C2	−0.8 (6)
N2—N1—C3—C2	1.2 (5)	C3—N1—N2—C1	−3.3 (5)
N2—N1—C3—C4	−176.1 (3)	C3—N1—C14—C19	56.4 (6)
N2—N1—C14—C19	−127.5 (5)	C3—N1—C14—C15	−123.7 (5)
N2—N1—C14—C15	52.4 (6)	C3—C2—C7—C6	0.6 (5)
N2—C1—C8—C9	172.9 (2)	C14—N1—N2—C1	−179.4 (2)
N2—C1—C8—C13	−6.7 (4)	C14—N1—C3—C2	176.9 (2)
N3—C1—C8—C9	−5.4 (4)	C14—N1—C3—C4	−0.5 (5)
N3—C1—C8—C13	175.0 (2)	C14—C19—C18—C17	−0.1 (9)
N3—C2—C7—C6	−179.0 (3)	C19—C14—C15—C16	−0.2 (9)
N3—C2—C3—N1	2.2 (5)	C19—C18—C17—C16	0.7 (9)
N3—C2—C3—C4	179.7 (4)	C18—C17—C16—C15	−1.1 (9)
C1—N3—C2—C7	176.4 (2)	C17—C16—C15—C14	0.8 (8)
C1—N3—C2—C3	−3.2 (5)	C15—C14—C19—C18	−0.2 (9)
C1—C8—C9—C10	−177.7 (3)	C8—C9—C10—C11	−2.6 (5)
C1—C8—C13—C12	179.4 (3)	C9—C8—C13—C12	−0.2 (5)
C2—N3—C1—N2	0.8 (5)	C9—C10—C11—C12	1.5 (5)
C2—N3—C1—C8	178.8 (3)	C10—C11—C12—C13	0.3 (5)
C2—C7—C6—C5	−0.5 (5)	C11—C12—C13—C8	−0.9 (5)
C7—C2—C3—N1	−177.4 (3)	C13—C8—C9—C10	2.0 (4)
C7—C2—C3—C4	0.1 (5)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20044_0m_4p7574GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.670 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.0607 (6) Å	Cell parameters from 2047 reflections
b = 6.0918 (4) Å	θ = 3.5–25.7°
c = 18.733 (3) Å	µ = 0.10 mm^−1
β = 99.951 (7)°	T = 271 K
V = 1130.84 (19) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	758 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	553 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.037
Detector resolution: 7.9 pixels mm^-1	θmax = 26.4°, θmin = 2.2°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0643 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.8964. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.668, Tmax = 0.745	l = −7→7
6290 measured reflections

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)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.062P)^2 + 0.2883P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
758 reflections	Δρmax = 0.12 e Å^−3
199 parameters	Δρmin = −0.15 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 4.7574 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.13 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C12 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.99 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.13 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.02 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.09 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 49 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 4 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4738 (3)	0.6808 (4)	0.6636 (4)	0.023 (4)
N2	0.4433 (3)	0.6638 (4)	0.7314 (4)	0.023 (4)
N3	0.2093 (3)	0.6601 (4)	0.6793 (4)	0.024 (4)
C1	0.3106 (3)	0.6602 (5)	0.7339 (5)	0.017 (4)
C2	0.2422 (4)	0.6650 (5)	0.6111 (5)	0.019 (4)
C7	0.1424 (3)	0.6543 (5)	0.5501 (5)	0.020 (4)
H7	0.052484	0.646924	0.555707	0.024*
C6	0.1737 (3)	0.6543 (5)	0.4817 (5)	0.021 (4)
H6	0.105376	0.643102	0.441526	0.025*
C5	0.3081 (3)	0.6712 (4)	0.4722 (4)	0.025 (4)
H5	0.328635	0.673012	0.425630	0.030*
C4	0.4101 (3)	0.6852 (5)	0.5312 (5)	0.023 (4)
H4	0.499515	0.697153	0.524910	0.027*
C3	0.3781 (3)	0.6812 (5)	0.6000 (4)	0.020 (4)
C14	0.6163 (2)	0.6855 (4)	0.6625 (4)	0.019 (4)
C19	0.6693 (3)	0.8531 (4)	0.6274 (4)	0.024 (5)
H19	0.613093	0.962185	0.604185	0.029*
C18	0.8060 (3)	0.8595 (5)	0.6266 (5)	0.030 (5)
H18	0.842481	0.973355	0.603131	0.036*
C17	0.8873 (3)	0.6987 (5)	0.6603 (4)	0.040 (5)
H17	0.979573	0.703050	0.659777	0.047*
C16	0.8343 (3)	0.5295 (5)	0.6952 (5)	0.035 (5)
H16	0.890765	0.419456	0.717513	0.042*
C15	0.6975 (3)	0.5221 (4)	0.6972 (4)	0.030 (5)
H15	0.661297	0.409560	0.721399	0.036*
C8	0.2788 (3)	0.6595 (5)	0.8078 (5)	0.020 (4)
C9	0.1442 (3)	0.6804 (5)	0.8168 (5)	0.023 (4)
H9	0.075347	0.686190	0.776712	0.028*
C10	0.1154 (4)	0.6924 (5)	0.8861 (4)	0.024 (4)
H10	0.026559	0.713327	0.892338	0.029*
C11	0.2143 (3)	0.6743 (4)	0.9456 (5)	0.029 (4)
H11	0.192330	0.679025	0.991789	0.035*
C12	0.3472 (3)	0.6488 (5)	0.9372 (5)	0.027 (4)
H12	0.414887	0.633049	0.977502	0.032*
C13	0.3783 (4)	0.6471 (5)	0.8684 (5)	0.023 (4)
H13	0.468157	0.637459	0.862687	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0179 (15)	0.0244 (12)	0.030 (11)	0.0000 (11)	0.010 (3)	0.002 (3)
N2	0.0180 (16)	0.0249 (12)	0.027 (11)	−0.0027 (10)	0.007 (3)	−0.002 (3)
N3	0.0190 (16)	0.0220 (12)	0.029 (12)	0.0006 (11)	−0.002 (3)	0.003 (3)
C1	0.0145 (16)	0.0135 (12)	0.021 (12)	0.0002 (11)	0.001 (3)	0.000 (3)
C2	0.0191 (19)	0.0119 (12)	0.026 (12)	0.0023 (12)	0.001 (3)	−0.001 (3)
C7	0.0157 (17)	0.0230 (14)	0.023 (13)	0.0030 (12)	0.008 (3)	0.001 (3)
C6	0.0205 (18)	0.0218 (14)	0.020 (13)	−0.0007 (12)	0.001 (4)	−0.007 (3)
C5	0.0266 (17)	0.0222 (13)	0.028 (12)	0.0002 (11)	0.007 (3)	0.004 (2)
C4	0.0183 (17)	0.0243 (13)	0.029 (12)	−0.0012 (13)	0.011 (3)	−0.004 (3)
C3	0.0130 (17)	0.0151 (12)	0.030 (12)	0.0005 (12)	0.001 (3)	−0.002 (3)
C14	0.0139 (13)	0.0273 (13)	0.015 (12)	−0.0008 (10)	0.002 (3)	−0.004 (2)
C19	0.0229 (15)	0.0286 (15)	0.021 (16)	−0.0007 (11)	0.004 (4)	−0.001 (2)
C18	0.0208 (15)	0.0463 (18)	0.025 (17)	−0.0096 (12)	0.009 (4)	0.001 (3)
C17	0.0133 (14)	0.064 (2)	0.040 (17)	0.0003 (14)	−0.001 (3)	−0.002 (3)
C16	0.0263 (16)	0.0485 (19)	0.026 (17)	0.0160 (14)	−0.004 (4)	0.003 (3)
C15	0.0242 (15)	0.0332 (16)	0.034 (15)	0.0040 (11)	0.007 (3)	0.000 (3)
C8	0.0197 (18)	0.0159 (13)	0.026 (12)	−0.0012 (12)	0.011 (3)	0.007 (3)
C9	0.0187 (18)	0.0186 (13)	0.034 (13)	−0.0008 (11)	0.007 (3)	0.002 (3)
C10	0.0207 (17)	0.0199 (13)	0.032 (13)	−0.0021 (13)	0.005 (3)	−0.003 (3)
C11	0.0320 (18)	0.0196 (13)	0.036 (14)	−0.0023 (12)	0.006 (4)	0.003 (3)
C12	0.0266 (19)	0.0223 (14)	0.031 (13)	0.0004 (12)	0.003 (4)	0.008 (3)
C13	0.0183 (17)	0.0219 (14)	0.030 (13)	−0.0008 (13)	0.005 (3)	0.003 (3)

Geometric parameters (Å, º)

N1—N2	1.362 (8)	C19—C18	1.379 (4)
N1—C3	1.396 (8)	C18—H18	0.9300
N1—C14	1.438 (4)	C18—C17	1.360 (6)
N2—C1	1.344 (4)	C17—H17	0.9300
N3—C1	1.313 (7)	C17—C16	1.376 (6)
N3—C2	1.376 (8)	C16—H16	0.9300
C1—C8	1.473 (8)	C16—C15	1.384 (4)
C2—C7	1.385 (8)	C15—H15	0.9300
C2—C3	1.421 (5)	C8—C9	1.399 (5)
C7—H7	0.9300	C8—C13	1.380 (8)
C7—C6	1.372 (8)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.380 (8)
C6—C5	1.397 (5)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.365 (8)
C5—C4	1.376 (7)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.382 (5)
C4—C3	1.382 (8)	C12—H12	0.9300
C14—C19	1.371 (5)	C12—C13	1.378 (9)
C14—C15	1.377 (5)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	124.2 (4)	C18—C19—H19	120.1
N2—N1—C14	113.6 (5)	C19—C18—H18	120.1
C3—N1—C14	122.1 (6)	C17—C18—C19	119.7 (4)
C1—N2—N1	114.8 (6)	C17—C18—H18	120.1
C1—N3—C2	116.4 (4)	C18—C17—H17	119.7
N2—C1—C8	114.3 (6)	C18—C17—C16	120.6 (3)
N3—C1—N2	128.0 (7)	C16—C17—H17	119.7
N3—C1—C8	117.8 (4)	C17—C16—H16	119.8
N3—C2—C7	120.6 (4)	C17—C16—C15	120.4 (4)
N3—C2—C3	121.9 (6)	C15—C16—H16	119.8
C7—C2—C3	117.5 (6)	C14—C15—C16	118.3 (4)
C2—C7—H7	119.4	C14—C15—H15	120.8
C6—C7—C2	121.3 (4)	C16—C15—H15	120.8
C6—C7—H7	119.4	C9—C8—C1	119.0 (6)
C7—C6—H6	119.9	C13—C8—C1	121.9 (4)
C7—C6—C5	120.2 (6)	C13—C8—C9	119.0 (7)
C5—C6—H6	119.9	C8—C9—H9	120.5
C6—C5—H5	119.8	C10—C9—C8	118.9 (6)
C4—C5—C6	120.4 (6)	C10—C9—H9	120.5
C4—C5—H5	119.8	C9—C10—H10	119.3
C5—C4—H4	120.4	C11—C10—C9	121.5 (4)
C5—C4—C3	119.2 (4)	C11—C10—H10	119.3
C3—C4—H4	120.4	C10—C11—H11	120.0
N1—C3—C2	114.5 (6)	C10—C11—C12	120.0 (7)
C4—C3—N1	123.9 (4)	C12—C11—H11	120.0
C4—C3—C2	121.5 (6)	C11—C12—H12	120.4
C19—C14—N1	119.5 (3)	C13—C12—C11	119.2 (6)
C19—C14—C15	121.1 (2)	C13—C12—H12	120.4
C15—C14—N1	119.4 (3)	C8—C13—H13	119.3
C14—C19—H19	120.1	C12—C13—C8	121.3 (4)
C14—C19—C18	119.8 (4)	C12—C13—H13	119.3
N1—N2—C1—N3	3.7 (5)	C7—C6—C5—C4	0.8 (4)
N1—N2—C1—C8	−175.4 (3)	C6—C5—C4—C3	0.3 (5)
N1—C14—C19—C18	179.5 (6)	C5—C4—C3—N1	175.9 (2)
N1—C14—C15—C16	179.7 (6)	C5—C4—C3—C2	−0.6 (6)
N2—N1—C3—C2	0.8 (5)	C3—N1—N2—C1	−3.9 (5)
N2—N1—C3—C4	−175.9 (3)	C3—N1—C14—C19	56.8 (6)
N2—N1—C14—C19	−126.6 (5)	C3—N1—C14—C15	−123.6 (6)
N2—N1—C14—C15	53.0 (6)	C3—C2—C7—C6	1.4 (5)
N2—C1—C8—C9	173.0 (2)	C14—N1—N2—C1	179.6 (2)
N2—C1—C8—C13	−4.5 (5)	C14—N1—C3—C2	177.0 (2)
N3—C1—C8—C9	−6.2 (4)	C14—N1—C3—C4	0.3 (5)
N3—C1—C8—C13	176.3 (2)	C14—C19—C18—C17	0.4 (10)
N3—C2—C7—C6	−178.6 (3)	C19—C14—C15—C16	−0.7 (9)
N3—C2—C3—N1	3.0 (5)	C19—C18—C17—C16	0.0 (10)
N3—C2—C3—C4	179.8 (3)	C18—C17—C16—C15	−0.8 (10)
C1—N3—C2—C7	176.8 (2)	C17—C16—C15—C14	1.1 (10)
C1—N3—C2—C3	−3.3 (5)	C15—C14—C19—C18	−0.1 (10)
C1—C8—C9—C10	−176.3 (3)	C8—C9—C10—C11	−3.0 (5)
C1—C8—C13—C12	179.3 (3)	C9—C8—C13—C12	1.8 (5)
C2—N3—C1—N2	−0.3 (5)	C9—C10—C11—C12	1.7 (5)
C2—N3—C1—C8	178.8 (3)	C10—C11—C12—C13	1.5 (5)
C2—C7—C6—C5	−1.7 (5)	C11—C12—C13—C8	−3.2 (6)
C7—C2—C3—N1	−177.1 (3)	C13—C8—C9—C10	1.3 (5)
C7—C2—C3—C4	−0.3 (5)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20048_0m_5p3456GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.700 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.0326 (6) Å	Cell parameters from 2046 reflections
b = 6.0553 (4) Å	θ = 3.6–25.8°
c = 18.571 (3) Å	µ = 0.10 mm^−1
β = 100.029 (7)°	T = 291 K
V = 1110.93 (19) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	748 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	537 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.043
Detector resolution: 7.9 pixels mm^-1	θmax = 26.3°, θmin = 2.2°
ω and φ scans	h = −12→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0995 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.8569. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.639, Tmax = 0.745	l = −7→7
6150 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0612P)^2 + 0.1943P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
748 reflections	Δρmax = 0.12 e Å^−3
199 parameters	Δρmin = −0.15 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 5.3436 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.02 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.04 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.13 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C10 3.17 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C13 3.18 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C12 3.19 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.94 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.12 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.01 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.05 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 49 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4747 (3)	0.6730 (4)	0.6663 (4)	0.032 (4)
N2	0.4441 (3)	0.6560 (4)	0.7347 (4)	0.032 (4)
N3	0.2092 (3)	0.6513 (4)	0.6816 (5)	0.031 (4)
C1	0.3109 (4)	0.6515 (5)	0.7367 (5)	0.025 (4)
C2	0.2421 (4)	0.6592 (5)	0.6129 (5)	0.028 (4)
C7	0.1426 (4)	0.6475 (5)	0.5516 (5)	0.029 (4)
H7	0.052453	0.636705	0.557170	0.035*
C6	0.1740 (3)	0.6514 (5)	0.4827 (5)	0.032 (4)
H6	0.105486	0.640807	0.442052	0.038*
C5	0.3091 (3)	0.6713 (4)	0.4731 (5)	0.032 (4)
H5	0.330092	0.675794	0.426325	0.038*
C4	0.4101 (4)	0.6841 (6)	0.5330 (5)	0.032 (4)
H4	0.499771	0.697537	0.526873	0.038*
C3	0.3790 (4)	0.6771 (5)	0.6023 (5)	0.030 (4)
C14	0.6173 (2)	0.6826 (4)	0.6646 (4)	0.025 (4)
C19	0.6680 (3)	0.8598 (4)	0.6325 (4)	0.032 (5)
H19	0.610407	0.971326	0.611430	0.038*
C18	0.8045 (3)	0.8720 (5)	0.6317 (5)	0.035 (6)
H18	0.839571	0.993269	0.610581	0.042*
C17	0.8883 (3)	0.7078 (5)	0.6617 (4)	0.038 (5)
H17	0.980488	0.716673	0.660689	0.046*
C16	0.8376 (3)	0.5281 (5)	0.6935 (5)	0.033 (5)
H16	0.895436	0.415210	0.713329	0.040*
C15	0.7007 (3)	0.5152 (4)	0.6959 (4)	0.033 (5)
H15	0.665785	0.396088	0.718228	0.039*
C8	0.2786 (4)	0.6527 (5)	0.8111 (5)	0.026 (4)
C9	0.1434 (3)	0.6759 (5)	0.8198 (5)	0.030 (4)
H9	0.074086	0.680775	0.779456	0.036*
C10	0.1159 (4)	0.6914 (5)	0.8899 (4)	0.031 (4)
H10	0.027105	0.715499	0.896116	0.037*
C11	0.2146 (3)	0.6725 (4)	0.9506 (5)	0.035 (4)
H11	0.192095	0.678390	0.997075	0.042*
C12	0.3482 (4)	0.6446 (5)	0.9423 (5)	0.033 (4)
H12	0.416358	0.629481	0.982931	0.039*
C13	0.3781 (4)	0.6397 (5)	0.8725 (5)	0.030 (4)
H13	0.468026	0.627187	0.866690	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0164 (16)	0.0254 (12)	0.057 (12)	0.0001 (11)	0.016 (3)	−0.001 (3)
N2	0.0184 (16)	0.0249 (12)	0.056 (12)	−0.0014 (10)	0.016 (3)	−0.002 (3)
N3	0.0169 (18)	0.0198 (12)	0.054 (12)	0.0006 (11)	0.001 (3)	−0.003 (3)
C1	0.0144 (17)	0.0143 (12)	0.046 (12)	0.0005 (12)	0.008 (3)	−0.002 (3)
C2	0.018 (2)	0.0146 (13)	0.052 (13)	0.0019 (13)	0.005 (4)	0.000 (4)
C7	0.0147 (18)	0.0219 (14)	0.049 (13)	0.0020 (12)	0.004 (3)	0.001 (3)
C6	0.023 (2)	0.0222 (14)	0.050 (13)	−0.0011 (13)	0.005 (4)	−0.003 (4)
C5	0.0248 (17)	0.0224 (14)	0.049 (13)	0.0004 (11)	0.009 (3)	0.000 (3)
C4	0.0202 (19)	0.0236 (13)	0.054 (12)	−0.0013 (13)	0.012 (4)	−0.003 (4)
C3	0.0181 (19)	0.0152 (13)	0.056 (12)	0.0017 (13)	0.007 (4)	0.001 (4)
C14	0.0142 (13)	0.0266 (13)	0.037 (13)	−0.0011 (10)	0.008 (3)	0.000 (2)
C19	0.0215 (16)	0.0313 (15)	0.041 (17)	−0.0013 (11)	0.003 (4)	0.003 (2)
C18	0.0231 (16)	0.0474 (18)	0.036 (19)	−0.0082 (12)	0.011 (4)	0.005 (3)
C17	0.0152 (15)	0.057 (2)	0.043 (17)	0.0011 (13)	0.005 (4)	−0.001 (3)
C16	0.0259 (16)	0.0452 (18)	0.027 (17)	0.0151 (13)	−0.003 (4)	0.001 (3)
C15	0.0252 (15)	0.0319 (16)	0.041 (16)	0.0035 (11)	0.007 (3)	0.000 (3)
C8	0.0164 (19)	0.0153 (12)	0.050 (12)	−0.0016 (12)	0.012 (4)	−0.004 (3)
C9	0.0195 (19)	0.0176 (13)	0.054 (14)	−0.0012 (12)	0.010 (4)	−0.003 (4)
C10	0.0209 (18)	0.0184 (14)	0.057 (14)	−0.0026 (13)	0.014 (4)	−0.004 (3)
C11	0.0292 (18)	0.0197 (13)	0.058 (14)	−0.0027 (12)	0.012 (4)	0.002 (3)
C12	0.028 (2)	0.0212 (14)	0.050 (13)	−0.0005 (13)	0.008 (4)	−0.002 (4)
C13	0.0184 (18)	0.0197 (13)	0.052 (13)	0.0014 (13)	0.009 (3)	−0.003 (3)

Geometric parameters (Å, º)

N1—N2	1.361 (8)	C19—C18	1.374 (4)
N1—C3	1.392 (8)	C18—H18	0.9300
N1—C14	1.438 (4)	C18—C17	1.357 (5)
N2—C1	1.344 (4)	C17—H17	0.9300
N3—C1	1.313 (7)	C17—C16	1.377 (5)
N3—C2	1.374 (8)	C16—H16	0.9300
C1—C8	1.473 (8)	C16—C15	1.385 (4)
C2—C7	1.379 (8)	C15—H15	0.9300
C2—C3	1.425 (5)	C8—C9	1.401 (5)
C7—H7	0.9300	C8—C13	1.381 (8)
C7—C6	1.372 (9)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.379 (8)
C6—C5	1.402 (5)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.370 (8)
C5—C4	1.370 (7)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.386 (5)
C4—C3	1.376 (8)	C12—H12	0.9300
C14—C19	1.367 (5)	C12—C13	1.381 (9)
C14—C15	1.377 (5)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	124.3 (4)	C18—C19—H19	120.2
N2—N1—C14	114.3 (6)	C19—C18—H18	119.9
C3—N1—C14	121.4 (6)	C17—C18—C19	120.2 (4)
C1—N2—N1	114.5 (6)	C17—C18—H18	119.9
C1—N3—C2	116.3 (4)	C18—C17—H17	119.8
N2—C1—C8	114.1 (6)	C18—C17—C16	120.4 (3)
N3—C1—N2	128.4 (7)	C16—C17—H17	119.8
N3—C1—C8	117.5 (4)	C17—C16—H16	120.0
N3—C2—C7	120.5 (4)	C17—C16—C15	120.1 (3)
N3—C2—C3	121.6 (6)	C15—C16—H16	120.0
C7—C2—C3	117.9 (7)	C14—C15—C16	118.5 (4)
C2—C7—H7	119.4	C14—C15—H15	120.7
C6—C7—C2	121.2 (4)	C16—C15—H15	120.7
C6—C7—H7	119.4	C9—C8—C1	119.0 (6)
C7—C6—H6	119.9	C13—C8—C1	121.9 (4)
C7—C6—C5	120.2 (6)	C13—C8—C9	119.1 (7)
C5—C6—H6	119.9	C8—C9—H9	120.9
C6—C5—H5	120.1	C10—C9—C8	118.2 (6)
C4—C5—C6	119.8 (7)	C10—C9—H9	120.9
C4—C5—H5	120.1	C9—C10—H10	118.8
C5—C4—H4	120.0	C11—C10—C9	122.4 (4)
C5—C4—C3	120.1 (4)	C11—C10—H10	118.8
C3—C4—H4	120.0	C10—C11—H11	120.2
N1—C3—C2	114.8 (6)	C10—C11—C12	119.5 (7)
C4—C3—N1	124.3 (4)	C12—C11—H11	120.2
C4—C3—C2	120.8 (6)	C11—C12—H12	120.7
C19—C14—N1	119.2 (3)	C13—C12—C11	118.6 (6)
C19—C14—C15	121.2 (2)	C13—C12—H12	120.7
C15—C14—N1	119.6 (3)	C8—C13—H13	119.0
C14—C19—H19	120.2	C12—C13—C8	122.0 (4)
C14—C19—C18	119.6 (3)	C12—C13—H13	119.0
N1—N2—C1—N3	3.4 (5)	C7—C6—C5—C4	0.8 (5)
N1—N2—C1—C8	−174.9 (3)	C6—C5—C4—C3	0.1 (5)
N1—C14—C19—C18	178.9 (6)	C5—C4—C3—N1	175.2 (2)
N1—C14—C15—C16	180.0 (6)	C5—C4—C3—C2	−0.8 (6)
N2—N1—C3—C2	−0.7 (5)	C3—N1—N2—C1	−2.5 (5)
N2—N1—C3—C4	−176.9 (3)	C3—N1—C14—C19	58.8 (6)
N2—N1—C14—C19	−122.4 (6)	C3—N1—C14—C15	−122.1 (6)
N2—N1—C14—C15	56.8 (6)	C3—C2—C7—C6	0.4 (5)
N2—C1—C8—C9	172.2 (2)	C14—N1—N2—C1	178.75 (19)
N2—C1—C8—C13	−5.5 (5)	C14—N1—C3—C2	178.1 (3)
N3—C1—C8—C9	−6.3 (4)	C14—N1—C3—C4	1.8 (6)
N3—C1—C8—C13	176.1 (2)	C14—C19—C18—C17	0.9 (10)
N3—C2—C7—C6	−178.9 (3)	C19—C14—C15—C16	−0.9 (10)
N3—C2—C3—N1	3.4 (5)	C19—C18—C17—C16	−0.4 (10)
N3—C2—C3—C4	179.8 (4)	C18—C17—C16—C15	−0.8 (10)
C1—N3—C2—C7	176.4 (2)	C17—C16—C15—C14	1.4 (10)
C1—N3—C2—C3	−2.8 (5)	C15—C14—C19—C18	−0.2 (10)
C1—C8—C9—C10	−175.8 (3)	C8—C9—C10—C11	−3.7 (6)
C1—C8—C13—C12	178.9 (3)	C9—C8—C13—C12	1.3 (5)
C2—N3—C1—N2	−0.8 (5)	C9—C10—C11—C12	2.3 (5)
C2—N3—C1—C8	177.4 (3)	C10—C11—C12—C13	0.9 (5)
C2—C7—C6—C5	−1.1 (6)	C11—C12—C13—C8	−2.7 (6)
C7—C2—C3—N1	−175.8 (3)	C13—C8—C9—C10	1.9 (5)
C7—C2—C3—C4	0.5 (5)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20050_0m_5p5393GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.718 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.0002 (5) Å	Cell parameters from 2189 reflections
b = 6.0842 (3) Å	θ = 3.5–25.8°
c = 18.352 (2) Å	µ = 0.10 mm^−1
β = 100.026 (6)°	T = 276 K
V = 1099.55 (15) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	734 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	545 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.032
Detector resolution: 7.9 pixels mm^-1	θmax = 26.3°, θmin = 2.2°
ω and φ scans	h = −11→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0585 before and 0.0406 after correction. The Ratio of minimum to maximum transmission is 0.8887. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.662, Tmax = 0.745	l = −7→7
4978 measured reflections

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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0375P)^2 + 0.580P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
734 reflections	Δρmax = 0.10 e Å^−3
199 parameters	Δρmin = −0.11 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 5.5393 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.02 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C10 3.16 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C13 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.93 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.16 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C6 ..C11 3.20 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.04 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.05 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C18 3.16 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C19 3.18 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 61 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 3 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 3 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4764 (3)	0.6682 (5)	0.6709 (4)	0.031 (4)
N2	0.4457 (3)	0.6527 (4)	0.7402 (4)	0.032 (4)
N3	0.2097 (3)	0.6447 (5)	0.6863 (4)	0.028 (4)
C1	0.3121 (3)	0.6477 (5)	0.7422 (5)	0.024 (4)
C2	0.2436 (3)	0.6532 (5)	0.6169 (5)	0.026 (4)
C7	0.1443 (3)	0.6404 (5)	0.5541 (5)	0.026 (4)
H7	0.053804	0.626691	0.559300	0.031*
C6	0.1763 (3)	0.6476 (6)	0.4847 (5)	0.029 (4)
H6	0.107954	0.636499	0.443467	0.035*
C5	0.3117 (3)	0.6717 (4)	0.4755 (5)	0.031 (4)
H5	0.333197	0.678639	0.428240	0.037*
C4	0.4124 (4)	0.6849 (6)	0.5364 (5)	0.031 (4)
H4	0.502336	0.701681	0.530563	0.037*
C3	0.3801 (3)	0.6734 (6)	0.6062 (5)	0.030 (4)
C14	0.6191 (2)	0.6869 (4)	0.6685 (4)	0.023 (4)
C19	0.6656 (3)	0.8792 (5)	0.6438 (4)	0.024 (5)
H19	0.605321	0.993302	0.628581	0.029*
C18	0.8015 (3)	0.9047 (5)	0.6412 (5)	0.035 (6)
H18	0.833242	1.035458	0.624246	0.042*
C17	0.8896 (3)	0.7356 (5)	0.6639 (4)	0.032 (5)
H17	0.981733	0.752205	0.662873	0.038*
C16	0.8423 (3)	0.5423 (5)	0.6882 (4)	0.026 (5)
H16	0.902543	0.427547	0.702695	0.031*
C15	0.7057 (3)	0.5156 (5)	0.6914 (4)	0.033 (5)
H15	0.673685	0.385385	0.708504	0.039*
C8	0.2795 (3)	0.6487 (5)	0.8176 (5)	0.025 (4)
C9	0.1447 (3)	0.6759 (5)	0.8266 (5)	0.032 (4)
H9	0.075078	0.682922	0.785780	0.039*
C10	0.1174 (4)	0.6921 (6)	0.8977 (4)	0.034 (4)
H10	0.028533	0.718222	0.904052	0.041*
C11	0.2162 (3)	0.6710 (4)	0.9591 (5)	0.036 (4)
H11	0.194278	0.677592	1.006230	0.043*
C12	0.3499 (3)	0.6398 (5)	0.9497 (5)	0.030 (4)
H12	0.418599	0.623347	0.990544	0.036*
C13	0.3792 (4)	0.6334 (5)	0.8792 (5)	0.027 (4)
H13	0.469175	0.618191	0.873140	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0153 (15)	0.0239 (13)	0.055 (11)	−0.0002 (11)	0.011 (3)	0.003 (3)
N2	0.0182 (16)	0.0244 (13)	0.056 (11)	−0.0024 (10)	0.014 (3)	−0.001 (3)
N3	0.0159 (16)	0.0196 (12)	0.048 (12)	0.0014 (11)	0.000 (3)	0.001 (3)
C1	0.0146 (17)	0.0130 (13)	0.044 (11)	0.0026 (12)	0.001 (3)	0.003 (3)
C2	0.0149 (18)	0.0147 (14)	0.048 (12)	−0.0007 (13)	0.001 (3)	−0.001 (4)
C7	0.0150 (17)	0.0185 (14)	0.045 (12)	−0.0007 (13)	0.005 (3)	−0.005 (4)
C6	0.0212 (18)	0.0222 (15)	0.043 (13)	0.0010 (13)	0.004 (4)	−0.002 (4)
C5	0.0236 (16)	0.0211 (14)	0.047 (12)	0.0001 (12)	0.004 (3)	0.002 (3)
C4	0.0177 (18)	0.0228 (14)	0.052 (12)	−0.0015 (14)	0.002 (4)	0.002 (4)
C3	0.0182 (18)	0.0147 (14)	0.055 (11)	−0.0002 (14)	0.004 (3)	0.003 (4)
C14	0.0144 (13)	0.0270 (14)	0.029 (13)	−0.0019 (11)	0.005 (3)	−0.003 (2)
C19	0.0189 (14)	0.0304 (16)	0.021 (17)	−0.0002 (11)	−0.002 (3)	0.004 (3)
C18	0.0223 (15)	0.0396 (18)	0.044 (19)	−0.0029 (12)	0.006 (4)	0.011 (3)
C17	0.0159 (14)	0.0454 (19)	0.034 (18)	0.0000 (12)	0.002 (3)	−0.003 (3)
C16	0.0237 (15)	0.0363 (18)	0.016 (17)	0.0117 (13)	−0.002 (3)	−0.003 (3)
C15	0.0257 (15)	0.0254 (16)	0.047 (17)	−0.0001 (11)	0.006 (3)	0.000 (3)
C8	0.0149 (18)	0.0142 (13)	0.045 (12)	−0.0015 (12)	0.004 (4)	−0.002 (3)
C9	0.0160 (18)	0.0197 (15)	0.061 (13)	−0.0025 (13)	0.005 (3)	0.002 (4)
C10	0.0193 (17)	0.0192 (14)	0.066 (13)	−0.0026 (13)	0.014 (3)	0.002 (4)
C11	0.0264 (17)	0.0185 (14)	0.065 (14)	−0.0022 (12)	0.013 (3)	0.001 (3)
C12	0.0238 (19)	0.0213 (15)	0.045 (13)	0.0020 (13)	0.005 (4)	−0.004 (4)
C13	0.0178 (17)	0.0192 (14)	0.045 (12)	0.0027 (13)	0.007 (3)	−0.002 (3)

Geometric parameters (Å, º)

N1—N2	1.361 (8)	C19—C18	1.376 (4)
N1—C3	1.393 (8)	C18—H18	0.9300
N1—C14	1.440 (4)	C18—C17	1.372 (5)
N2—C1	1.343 (4)	C17—H17	0.9300
N3—C1	1.317 (7)	C17—C16	1.371 (5)
N3—C2	1.375 (8)	C16—H16	0.9300
C1—C8	1.475 (8)	C16—C15	1.387 (4)
C2—C7	1.386 (8)	C15—H15	0.9300
C2—C3	1.418 (5)	C8—C9	1.397 (5)
C7—H7	0.9300	C8—C13	1.375 (8)
C7—C6	1.367 (9)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.383 (8)
C6—C5	1.402 (5)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.369 (8)
C5—C4	1.370 (7)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.390 (5)
C4—C3	1.377 (8)	C12—H12	0.9300
C14—C19	1.365 (5)	C12—C13	1.375 (9)
C14—C15	1.374 (4)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	124.2 (4)	C18—C19—H19	119.9
N2—N1—C14	114.8 (6)	C19—C18—H18	120.3
C3—N1—C14	120.9 (6)	C17—C18—C19	119.4 (3)
C1—N2—N1	114.5 (6)	C17—C18—H18	120.3
C1—N3—C2	115.9 (4)	C18—C17—H17	119.9
N2—C1—C8	114.2 (6)	C16—C17—C18	120.2 (2)
N3—C1—N2	128.4 (7)	C16—C17—H17	119.9
N3—C1—C8	117.5 (4)	C17—C16—H16	119.6
N3—C2—C7	120.8 (4)	C17—C16—C15	120.8 (3)
N3—C2—C3	122.0 (6)	C15—C16—H16	119.6
C7—C2—C3	117.2 (7)	C14—C15—C16	118.2 (3)
C2—C7—H7	119.2	C14—C15—H15	120.9
C6—C7—C2	121.5 (4)	C16—C15—H15	120.9
C6—C7—H7	119.2	C9—C8—C1	119.1 (6)
C7—C6—H6	119.9	C13—C8—C1	121.6 (4)
C7—C6—C5	120.3 (6)	C13—C8—C9	119.2 (7)
C5—C6—H6	119.9	C8—C9—H9	120.9
C6—C5—H5	120.1	C10—C9—C8	118.3 (6)
C4—C5—C6	119.7 (7)	C10—C9—H9	120.9
C4—C5—H5	120.1	C9—C10—H10	118.7
C5—C4—H4	120.1	C11—C10—C9	122.5 (4)
C5—C4—C3	119.9 (4)	C11—C10—H10	118.7
C3—C4—H4	120.1	C10—C11—H11	120.6
N1—C3—C2	114.8 (6)	C10—C11—C12	118.9 (7)
C4—C3—N1	123.7 (4)	C12—C11—H11	120.6
C4—C3—C2	121.4 (6)	C11—C12—H12	120.4
C19—C14—N1	118.4 (3)	C13—C12—C11	119.2 (6)
C19—C14—C15	121.2 (2)	C13—C12—H12	120.4
C15—C14—N1	120.4 (3)	C8—C13—H13	119.0
C14—C19—H19	119.9	C12—C13—C8	121.9 (4)
C14—C19—C18	120.2 (3)	C12—C13—H13	119.0
N1—N2—C1—N3	3.7 (5)	C7—C6—C5—C4	0.9 (5)
N1—N2—C1—C8	−175.4 (3)	C6—C5—C4—C3	0.3 (5)
N1—C14—C19—C18	179.4 (7)	C5—C4—C3—N1	174.8 (2)
N1—C14—C15—C16	−179.7 (7)	C5—C4—C3—C2	−1.5 (6)
N2—N1—C3—C2	−2.2 (5)	C3—N1—N2—C1	−1.5 (5)
N2—N1—C3—C4	−178.7 (4)	C3—N1—C14—C19	64.8 (7)
N2—N1—C14—C19	−113.2 (6)	C3—N1—C14—C15	−115.9 (6)
N2—N1—C14—C15	66.0 (7)	C3—C2—C7—C6	−0.2 (5)
N2—C1—C8—C9	170.8 (3)	C14—N1—N2—C1	176.5 (2)
N2—C1—C8—C13	−6.3 (5)	C14—N1—C3—C2	180.0 (3)
N3—C1—C8—C9	−8.4 (5)	C14—N1—C3—C4	3.4 (6)
N3—C1—C8—C13	174.5 (2)	C14—C19—C18—C17	−0.2 (11)
N3—C2—C7—C6	−179.7 (4)	C19—C14—C15—C16	−0.5 (10)
N3—C2—C3—N1	4.3 (5)	C19—C18—C17—C16	0.7 (11)
N3—C2—C3—C4	−179.0 (4)	C18—C17—C16—C15	−1.1 (11)
C1—N3—C2—C7	176.9 (2)	C17—C16—C15—C14	1.0 (10)
C1—N3—C2—C3	−2.6 (5)	C15—C14—C19—C18	0.1 (11)
C1—C8—C9—C10	−175.5 (4)	C8—C9—C10—C11	−3.5 (6)
C1—C8—C13—C12	178.4 (3)	C9—C8—C13—C12	1.3 (6)
C2—N3—C1—N2	−1.7 (5)	C9—C10—C11—C12	2.3 (6)
C2—N3—C1—C8	177.4 (3)	C10—C11—C12—C13	0.7 (5)
C2—C7—C6—C5	−1.0 (6)	C11—C12—C13—C8	−2.5 (6)
C7—C2—C3—N1	−175.2 (3)	C13—C8—C9—C10	1.7 (5)
C7—C2—C3—C4	1.5 (6)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20052_0m_5p7631GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.729 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.9832 (7) Å	Cell parameters from 2090 reflections
b = 6.0752 (4) Å	θ = 3.5–25.8°
c = 18.290 (3) Å	µ = 0.11 mm^−1
β = 100.005 (9)°	T = 276 K
V = 1092.4 (2) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	736 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	535 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.037
Detector resolution: 7.9 pixels mm^-1	θmax = 26.3°, θmin = 2.2°
ω and φ scans	h = −11→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1389 before and 0.0678 after correction. The Ratio of minimum to maximum transmission is 0.9054. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.675, Tmax = 0.745	l = −7→7
5042 measured reflections

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0737P)^2 + 0.2439P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
736 reflections	Δρmax = 0.13 e Å^−3
199 parameters	Δρmin = −0.15 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 5.7631 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.01 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C10 3.16 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C13 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C9 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.93 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.15 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C6 ..C11 3.18 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.03 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.05 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C18 3.11 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C19 3.13 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 55 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4768 (4)	0.6672 (5)	0.6719 (5)	0.040 (4)
N2	0.4460 (3)	0.6539 (5)	0.7411 (5)	0.041 (4)
N3	0.2098 (4)	0.6435 (5)	0.6870 (5)	0.038 (4)
C1	0.3127 (4)	0.6474 (5)	0.7427 (5)	0.032 (4)
C2	0.2430 (4)	0.6520 (6)	0.6172 (5)	0.037 (4)
C7	0.1440 (4)	0.6398 (6)	0.5546 (5)	0.035 (5)
H7	0.053241	0.627084	0.559680	0.042*
C6	0.1768 (4)	0.6462 (6)	0.4851 (6)	0.040 (4)
H6	0.108379	0.633530	0.443690	0.047*
C5	0.3115 (4)	0.6715 (4)	0.4754 (5)	0.040 (4)
H5	0.332754	0.679270	0.427932	0.048*
C4	0.4125 (4)	0.6847 (6)	0.5367 (5)	0.039 (4)
H4	0.502668	0.701223	0.530793	0.047*
C3	0.3803 (4)	0.6736 (6)	0.6070 (5)	0.038 (4)
C14	0.6197 (3)	0.6883 (5)	0.6701 (5)	0.032 (5)
C19	0.6655 (3)	0.8844 (5)	0.6463 (5)	0.035 (6)
H19	0.604648	0.998757	0.632087	0.043*
C18	0.8014 (3)	0.9119 (6)	0.6434 (5)	0.051 (7)
H18	0.832834	1.044851	0.627696	0.061*
C17	0.8901 (3)	0.7413 (5)	0.6640 (5)	0.044 (6)
H17	0.982039	0.758666	0.662151	0.052*
C16	0.8436 (3)	0.5447 (5)	0.6872 (5)	0.042 (6)
H16	0.904203	0.429409	0.700510	0.050*
C15	0.7074 (3)	0.5168 (5)	0.6910 (5)	0.044 (6)
H15	0.675996	0.384653	0.707379	0.052*
C8	0.2791 (4)	0.6481 (5)	0.8185 (5)	0.033 (4)
C9	0.1450 (4)	0.6762 (6)	0.8284 (5)	0.037 (5)
H9	0.075015	0.684127	0.787609	0.045*
C10	0.1176 (4)	0.6921 (6)	0.8994 (5)	0.039 (5)
H10	0.028634	0.718576	0.905829	0.047*
C11	0.2164 (4)	0.6704 (5)	0.9607 (5)	0.039 (5)
H11	0.194379	0.677076	1.008055	0.047*
C12	0.3506 (4)	0.6382 (6)	0.9514 (6)	0.037 (5)
H12	0.419409	0.620323	0.992314	0.045*
C13	0.3792 (4)	0.6333 (6)	0.8806 (5)	0.034 (4)
H13	0.469279	0.619505	0.874386	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0185 (18)	0.0239 (15)	0.079 (13)	0.0001 (13)	0.017 (3)	−0.001 (3)
N2	0.0194 (19)	0.0248 (14)	0.081 (13)	−0.0006 (12)	0.016 (3)	−0.003 (3)
N3	0.021 (2)	0.0186 (14)	0.074 (13)	0.0005 (13)	0.005 (4)	0.002 (3)
C1	0.015 (2)	0.0125 (15)	0.068 (13)	0.0001 (14)	0.008 (4)	0.000 (4)
C2	0.019 (2)	0.0172 (16)	0.076 (13)	0.0010 (16)	0.010 (4)	−0.002 (4)
C7	0.0144 (19)	0.0196 (16)	0.073 (14)	0.0029 (14)	0.011 (4)	−0.003 (4)
C6	0.024 (2)	0.0211 (16)	0.074 (14)	−0.0002 (15)	0.012 (4)	−0.006 (4)
C5	0.023 (2)	0.0220 (16)	0.073 (14)	0.0002 (13)	0.005 (4)	0.000 (3)
C4	0.020 (2)	0.0229 (16)	0.075 (13)	−0.0032 (15)	0.009 (4)	−0.002 (4)
C3	0.020 (2)	0.0167 (16)	0.078 (13)	0.0016 (16)	0.009 (4)	0.004 (4)
C14	0.0156 (16)	0.0272 (16)	0.055 (15)	−0.0008 (12)	0.012 (3)	−0.005 (3)
C19	0.0204 (18)	0.0288 (19)	0.06 (2)	−0.0011 (12)	0.004 (4)	0.002 (3)
C18	0.0230 (18)	0.036 (2)	0.10 (2)	−0.0029 (14)	0.014 (4)	0.010 (3)
C17	0.0181 (17)	0.042 (2)	0.07 (2)	−0.0003 (14)	0.010 (4)	−0.006 (3)
C16	0.0257 (17)	0.034 (2)	0.063 (19)	0.0101 (14)	0.004 (4)	−0.008 (3)
C15	0.0228 (17)	0.0248 (18)	0.083 (19)	0.0008 (12)	0.008 (4)	0.001 (3)
C8	0.013 (2)	0.0158 (15)	0.071 (13)	0.0001 (13)	0.008 (4)	0.003 (4)
C9	0.021 (2)	0.0183 (16)	0.073 (15)	−0.0043 (14)	0.008 (4)	0.004 (4)
C10	0.019 (2)	0.0208 (16)	0.080 (15)	−0.0005 (15)	0.017 (4)	0.006 (4)
C11	0.029 (2)	0.0191 (16)	0.073 (16)	−0.0003 (13)	0.022 (4)	0.005 (3)
C12	0.026 (2)	0.0227 (17)	0.064 (14)	0.0025 (14)	0.014 (4)	−0.003 (4)
C13	0.020 (2)	0.0179 (16)	0.066 (14)	0.0020 (15)	0.013 (4)	−0.002 (4)

Geometric parameters (Å, º)

N1—N2	1.356 (9)	C19—C18	1.377 (4)
N1—C3	1.392 (8)	C18—H18	0.9300
N1—C14	1.438 (4)	C18—C17	1.372 (5)
N2—C1	1.337 (5)	C17—H17	0.9300
N3—C1	1.316 (7)	C17—C16	1.375 (5)
N3—C2	1.374 (8)	C16—H16	0.9300
C1—C8	1.481 (8)	C16—C15	1.384 (4)
C2—C7	1.380 (8)	C15—H15	0.9300
C2—C3	1.420 (6)	C8—C9	1.392 (6)
C7—H7	0.9300	C8—C13	1.380 (8)
C7—C6	1.367 (9)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.377 (9)
C6—C5	1.396 (6)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.365 (8)
C5—C4	1.373 (8)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.394 (5)
C4—C3	1.381 (9)	C12—H12	0.9300
C14—C19	1.374 (5)	C12—C13	1.373 (9)
C14—C15	1.372 (4)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	124.1 (4)	C18—C19—H19	119.9
N2—N1—C14	114.4 (6)	C19—C18—H18	120.3
C3—N1—C14	121.4 (7)	C17—C18—C19	119.4 (4)
C1—N2—N1	114.2 (7)	C17—C18—H18	120.3
C1—N3—C2	115.9 (5)	C18—C17—H17	119.9
N2—C1—C8	114.1 (7)	C18—C17—C16	120.3 (3)
N3—C1—N2	129.0 (8)	C16—C17—H17	119.9
N3—C1—C8	116.9 (5)	C17—C16—H16	119.7
N3—C2—C7	121.0 (4)	C17—C16—C15	120.6 (3)
N3—C2—C3	121.3 (7)	C15—C16—H16	119.7
C7—C2—C3	117.7 (7)	C14—C15—C16	118.6 (4)
C2—C7—H7	119.4	C14—C15—H15	120.7
C6—C7—C2	121.2 (5)	C16—C15—H15	120.7
C6—C7—H7	119.4	C9—C8—C1	120.0 (7)
C7—C6—H6	119.6	C13—C8—C1	121.4 (4)
C7—C6—C5	120.8 (7)	C13—C8—C9	118.4 (7)
C5—C6—H6	119.6	C8—C9—H9	120.5
C6—C5—H5	120.3	C10—C9—C8	119.0 (7)
C4—C5—C6	119.4 (7)	C10—C9—H9	120.5
C4—C5—H5	120.3	C9—C10—H10	118.8
C5—C4—H4	120.0	C11—C10—C9	122.4 (4)
C5—C4—C3	120.0 (4)	C11—C10—H10	118.8
C3—C4—H4	120.0	C10—C11—H11	120.5
N1—C3—C2	115.2 (7)	C10—C11—C12	119.1 (7)
C4—C3—N1	123.8 (5)	C12—C11—H11	120.5
C4—C3—C2	120.9 (7)	C11—C12—H12	120.7
C19—C14—N1	118.1 (3)	C13—C12—C11	118.7 (7)
C15—C14—N1	120.9 (3)	C13—C12—H12	120.7
C15—C14—C19	121.0 (3)	C8—C13—H13	118.8
C14—C19—H19	119.9	C12—C13—C8	122.4 (5)
C14—C19—C18	120.1 (3)	C12—C13—H13	118.8
N1—N2—C1—N3	3.0 (5)	C7—C6—C5—C4	1.6 (5)
N1—N2—C1—C8	−176.1 (3)	C6—C5—C4—C3	−0.2 (6)
N1—C14—C19—C18	−179.8 (8)	C5—C4—C3—N1	174.5 (3)
N1—C14—C15—C16	179.1 (8)	C5—C4—C3—C2	−1.0 (7)
N2—N1—C3—C2	−3.6 (6)	C3—N1—N2—C1	−0.1 (6)
N2—N1—C3—C4	−179.3 (4)	C3—N1—C14—C19	64.9 (8)
N2—N1—C14—C19	−111.5 (7)	C3—N1—C14—C15	−114.6 (7)
N2—N1—C14—C15	69.0 (8)	C3—C2—C7—C6	0.6 (6)
N2—C1—C8—C9	170.0 (3)	C14—N1—N2—C1	176.3 (2)
N2—C1—C8—C13	−6.4 (5)	C14—N1—C3—C2	−179.7 (3)
N3—C1—C8—C9	−9.2 (5)	C14—N1—C3—C4	4.6 (6)
N3—C1—C8—C13	174.4 (3)	C14—C19—C18—C17	0.5 (12)
N3—C2—C7—C6	−179.4 (4)	C19—C14—C15—C16	−0.4 (12)
N3—C2—C3—N1	5.0 (6)	C19—C18—C17—C16	0.0 (12)
N3—C2—C3—C4	−179.2 (4)	C18—C17—C16—C15	−0.7 (12)
C1—N3—C2—C7	177.3 (3)	C17—C16—C15—C14	0.9 (12)
C1—N3—C2—C3	−2.7 (6)	C15—C14—C19—C18	−0.3 (12)
C1—C8—C9—C10	−175.4 (4)	C8—C9—C10—C11	−3.3 (7)
C1—C8—C13—C12	178.6 (3)	C9—C8—C13—C12	2.2 (6)
C2—N3—C1—N2	−1.6 (6)	C9—C10—C11—C12	2.1 (6)
C2—N3—C1—C8	177.5 (3)	C10—C11—C12—C13	1.2 (5)
C2—C7—C6—C5	−1.8 (6)	C11—C12—C13—C8	−3.3 (6)
C7—C2—C3—N1	−175.0 (3)	C13—C8—C9—C10	1.1 (6)
C7—C2—C3—C4	0.8 (6)

1,3-Diphenyl-1,2,4-benzotriazin-4(1H)-yl (mo_sp20053_0m_6p0711GPa)

Crystal data

C19H14N3	F(000) = 596
Mr = 284.33	Dx = 1.739 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.9663 (7) Å	Cell parameters from 1909 reflections
b = 6.0642 (4) Å	θ = 3.6–25.9°
c = 18.252 (3) Å	µ = 0.11 mm^−1
β = 100.025 (9)°	T = 273 K
V = 1086.3 (2) Å^3	Block, clear dark brown
Z = 4	0.16 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 area detector diffractometer	727 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	481 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.057
Detector resolution: 7.9 pixels mm^-1	θmax = 26.4°, θmin = 3.6°
ω and φ scans	h = −11→12
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1695 before and 0.0802 after correction. The Ratio of minimum to maximum transmission is 0.7794. The λ/2 correction factor is Not present.	k = −7→7
Tmin = 0.581, Tmax = 0.745	l = −7→8
5236 measured reflections

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)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.140	w = 1/[σ^2(Fo^2) + (0.1083P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
727 reflections	Δρmax = 0.16 e Å^−3
199 parameters	Δρmin = −0.14 e Å^−3
231 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. High pressure data collection in a diamond anvil cell. 6.0711 GPa.

PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.11 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT199_ALERT_1_G Reported _cell_measurement_temperature ···.. (K) 273 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ···.. (K) 273 Check PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.01 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C10 3.15 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C13 3.16 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C9 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.92 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.15 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C6 ..C11 3.16 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.03 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.04 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C11 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C18 3.11 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C19 3.12 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C16 ..C19 3.18 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check

Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376.

PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 3 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 72 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 3 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 12 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 14 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 14 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info

No action taken.

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

	x	y	z	Uiso*/Ueq
N1	0.4773 (4)	0.6675 (6)	0.6728 (5)	0.034 (5)
N2	0.4457 (3)	0.6538 (5)	0.7417 (5)	0.036 (4)
N3	0.2093 (4)	0.6430 (6)	0.6877 (5)	0.035 (5)
C1	0.3125 (5)	0.6471 (6)	0.7441 (6)	0.032 (4)
C2	0.2440 (5)	0.6521 (7)	0.6182 (6)	0.035 (5)
C7	0.1447 (5)	0.6387 (6)	0.5548 (6)	0.033 (5)
H7	0.053919	0.624329	0.560047	0.040*
C6	0.1763 (4)	0.6461 (7)	0.4845 (6)	0.040 (5)
H6	0.108403	0.634418	0.442755	0.047*
C5	0.3125 (4)	0.6717 (5)	0.4772 (6)	0.034 (5)
H5	0.334595	0.680610	0.429833	0.041*
C4	0.4138 (5)	0.6837 (7)	0.5376 (6)	0.034 (5)
H4	0.504045	0.698581	0.531440	0.041*
C3	0.3813 (4)	0.6738 (7)	0.6078 (6)	0.032 (5)
C14	0.6200 (3)	0.6885 (5)	0.6695 (5)	0.032 (5)
C19	0.6653 (3)	0.8872 (6)	0.6474 (5)	0.033 (7)
H19	0.604207	1.002508	0.634468	0.040*
C18	0.8018 (3)	0.9157 (6)	0.6445 (6)	0.037 (7)
H18	0.833477	1.050135	0.629798	0.044*
C17	0.8899 (3)	0.7437 (6)	0.6634 (5)	0.026 (6)
H17	0.981369	0.760391	0.659964	0.031*
C16	0.8451 (3)	0.5468 (6)	0.6875 (5)	0.033 (6)
H16	0.906872	0.433666	0.702341	0.040*
C15	0.7079 (3)	0.5162 (5)	0.6896 (5)	0.037 (7)
H15	0.676244	0.381940	0.704339	0.045*
C8	0.2796 (4)	0.6484 (6)	0.8201 (5)	0.033 (5)
C9	0.1446 (4)	0.6749 (6)	0.8285 (6)	0.040 (5)
H9	0.074622	0.680410	0.787562	0.048*
C10	0.1183 (5)	0.6926 (7)	0.9001 (5)	0.040 (6)
H10	0.029304	0.720682	0.906480	0.047*
C11	0.2166 (4)	0.6711 (5)	0.9623 (6)	0.045 (6)
H11	0.194385	0.678202	1.009615	0.054*
C12	0.3506 (4)	0.6382 (7)	0.9527 (7)	0.040 (5)
H12	0.419574	0.620678	0.993659	0.049*
C13	0.3797 (5)	0.6319 (7)	0.8816 (6)	0.036 (5)
H13	0.469800	0.616092	0.875292	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0169 (19)	0.0304 (17)	0.055 (14)	0.0003 (14)	0.007 (3)	0.000 (3)
N2	0.021 (2)	0.0313 (17)	0.057 (14)	−0.0035 (13)	0.010 (4)	−0.003 (4)
N3	0.022 (2)	0.0222 (16)	0.060 (14)	−0.0006 (14)	0.002 (4)	−0.001 (4)
C1	0.019 (2)	0.0172 (17)	0.059 (14)	−0.0002 (16)	0.006 (4)	−0.002 (4)
C2	0.019 (2)	0.0212 (18)	0.063 (14)	0.0004 (17)	0.005 (4)	0.002 (5)
C7	0.019 (2)	0.0224 (18)	0.060 (15)	−0.0009 (17)	0.010 (4)	−0.005 (4)
C6	0.027 (3)	0.029 (2)	0.065 (15)	0.0021 (17)	0.015 (5)	0.004 (5)
C5	0.029 (2)	0.0284 (19)	0.045 (15)	−0.0030 (16)	0.006 (4)	0.000 (3)
C4	0.023 (2)	0.0291 (19)	0.052 (14)	−0.0031 (17)	0.009 (4)	−0.009 (4)
C3	0.020 (2)	0.0218 (18)	0.054 (14)	0.0016 (17)	0.004 (4)	−0.004 (4)
C14	0.0180 (18)	0.0309 (19)	0.046 (17)	−0.0030 (13)	0.007 (4)	−0.006 (3)
C19	0.026 (2)	0.034 (2)	0.04 (2)	0.0015 (15)	0.001 (5)	0.010 (3)
C18	0.024 (2)	0.037 (2)	0.05 (2)	−0.0032 (15)	0.001 (4)	0.006 (3)
C17	0.0212 (19)	0.047 (2)	0.01 (2)	−0.0008 (15)	−0.002 (4)	−0.008 (3)
C16	0.0273 (19)	0.041 (2)	0.03 (2)	0.0130 (16)	0.001 (4)	−0.003 (3)
C15	0.027 (2)	0.028 (2)	0.06 (2)	−0.0010 (14)	0.009 (4)	−0.003 (3)
C8	0.017 (2)	0.0207 (18)	0.060 (14)	−0.0008 (16)	0.005 (4)	−0.004 (4)
C9	0.022 (3)	0.0245 (19)	0.077 (17)	−0.0032 (16)	0.014 (4)	−0.006 (4)
C10	0.024 (2)	0.0205 (18)	0.076 (18)	−0.0012 (17)	0.015 (4)	−0.001 (4)
C11	0.028 (2)	0.0223 (18)	0.083 (18)	−0.0003 (15)	0.004 (5)	0.000 (3)
C12	0.031 (3)	0.0258 (19)	0.064 (15)	0.0030 (17)	0.009 (5)	−0.005 (5)
C13	0.023 (2)	0.0236 (18)	0.062 (15)	0.0024 (18)	0.007 (4)	−0.005 (4)

Geometric parameters (Å, º)

N1—N2	1.350 (9)	C19—C18	1.383 (5)
N1—C3	1.389 (8)	C18—H18	0.9300
N1—C14	1.439 (5)	C18—C17	1.368 (5)
N2—C1	1.336 (6)	C17—H17	0.9300
N3—C1	1.323 (8)	C17—C16	1.374 (6)
N3—C2	1.374 (8)	C16—H16	0.9300
C1—C8	1.481 (8)	C16—C15	1.387 (5)
C2—C7	1.388 (8)	C15—H15	0.9300
C2—C3	1.420 (7)	C8—C9	1.390 (6)
C7—H7	0.9300	C8—C13	1.370 (8)
C7—C6	1.373 (9)	C9—H9	0.9300
C6—H6	0.9300	C9—C10	1.381 (9)
C6—C5	1.396 (6)	C10—H10	0.9300
C5—H5	0.9300	C10—C11	1.370 (8)
C5—C4	1.360 (8)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.391 (6)
C4—C3	1.377 (9)	C12—H12	0.9300
C14—C19	1.372 (5)	C12—C13	1.377 (9)
C14—C15	1.372 (5)	C13—H13	0.9300
C19—H19	0.9300
N2—N1—C3	124.0 (5)	C18—C19—H19	120.1
N2—N1—C14	115.9 (7)	C19—C18—H18	120.4
C3—N1—C14	120.0 (7)	C17—C18—C19	119.2 (4)
C1—N2—N1	115.2 (7)	C17—C18—H18	120.4
C1—N3—C2	115.5 (5)	C18—C17—H17	119.5
N2—C1—C8	114.5 (7)	C18—C17—C16	120.9 (3)
N3—C1—N2	128.2 (8)	C16—C17—H17	119.5
N3—C1—C8	117.3 (5)	C17—C16—H16	119.9
N3—C2—C7	120.6 (5)	C17—C16—C15	120.1 (4)
N3—C2—C3	122.0 (7)	C15—C16—H16	119.9
C7—C2—C3	117.3 (7)	C14—C15—C16	118.5 (4)
C2—C7—H7	119.0	C14—C15—H15	120.7
C6—C7—C2	122.0 (5)	C16—C15—H15	120.7
C6—C7—H7	119.0	C9—C8—C1	118.8 (7)
C7—C6—H6	120.7	C13—C8—C1	121.3 (5)
C7—C6—C5	118.6 (8)	C13—C8—C9	119.9 (8)
C5—C6—H6	120.7	C8—C9—H9	121.3
C6—C5—H5	119.2	C10—C9—C8	117.4 (7)
C4—C5—C6	121.7 (8)	C10—C9—H9	121.3
C4—C5—H5	119.2	C9—C10—H10	118.3
C5—C4—H4	120.3	C11—C10—C9	123.4 (5)
C5—C4—C3	119.4 (5)	C11—C10—H10	118.3
C3—C4—H4	120.3	C10—C11—H11	120.9
N1—C3—C2	114.9 (7)	C10—C11—C12	118.3 (8)
C4—C3—N1	123.9 (5)	C12—C11—H11	120.9
C4—C3—C2	121.1 (7)	C11—C12—H12	120.4
C19—C14—N1	117.9 (3)	C13—C12—C11	119.1 (8)
C19—C14—C15	121.3 (3)	C13—C12—H12	120.4
C15—C14—N1	120.7 (4)	C8—C13—C12	121.8 (6)
C14—C19—H19	120.1	C8—C13—H13	119.1
C14—C19—C18	119.9 (3)	C12—C13—H13	119.1
N1—N2—C1—N3	3.1 (6)	C7—C6—C5—C4	1.6 (6)
N1—N2—C1—C8	−175.8 (4)	C6—C5—C4—C3	−0.9 (6)
N1—C14—C19—C18	179.0 (8)	C5—C4—C3—N1	174.8 (3)
N1—C14—C15—C16	−178.1 (8)	C5—C4—C3—C2	−0.3 (7)
N2—N1—C3—C2	−3.4 (6)	C3—N1—N2—C1	−0.2 (6)
N2—N1—C3—C4	−178.8 (4)	C3—N1—C14—C19	67.3 (8)
N2—N1—C14—C19	−109.4 (8)	C3—N1—C14—C15	−114.4 (8)
N2—N1—C14—C15	68.9 (9)	C3—C2—C7—C6	−0.1 (7)
N2—C1—C8—C9	170.5 (3)	C14—N1—N2—C1	176.4 (3)
N2—C1—C8—C13	−7.2 (6)	C14—N1—C3—C2	−179.8 (3)
N3—C1—C8—C9	−8.4 (6)	C14—N1—C3—C4	4.8 (7)
N3—C1—C8—C13	173.9 (3)	C14—C19—C18—C17	0.3 (13)
N3—C2—C7—C6	−179.6 (4)	C19—C14—C15—C16	0.2 (14)
N3—C2—C3—N1	4.8 (6)	C19—C18—C17—C16	−2.1 (13)
N3—C2—C3—C4	−179.7 (5)	C18—C17—C16—C15	3.0 (13)
C1—N3—C2—C7	177.0 (3)	C17—C16—C15—C14	−2.0 (13)
C1—N3—C2—C3	−2.5 (6)	C15—C14—C19—C18	0.7 (14)
C1—C8—C9—C10	−175.1 (4)	C8—C9—C10—C11	−4.4 (7)
C1—C8—C13—C12	178.5 (4)	C9—C8—C13—C12	0.8 (7)
C2—N3—C1—N2	−1.7 (6)	C9—C10—C11—C12	2.6 (6)
C2—N3—C1—C8	177.1 (4)	C10—C11—C12—C13	1.0 (6)
C2—C7—C6—C5	−1.1 (7)	C11—C12—C13—C8	−2.6 (7)
C7—C2—C3—N1	−174.8 (4)	C13—C8—C9—C10	2.6 (6)
C7—C2—C3—C4	0.8 (6)