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Nicotinic acid (NA), known as vitamin B3, has been widely studied in pharmaceutical science. Herein, three salts derived from NA and (1R,2R)-1,2-di­phenyl­ethyl­enedi­amine (DPEN), including one solvent-free salt (DPEN)(NA)2 and two solvated salts, (DPEN)(NA)2(EA) and (DPEN)(NA)2(ACN) (EA: ethyl acetate, ACN: aceto­nitrile), have been obtained and characterized by solid-state techniques. By the investigation of single-crystal structures, the synthons, acid–ammonium heterodimer and Nammonium—H...Npyridine between functional groups of 1,2-di­phenyl­ethyl­enedi­ammonium and NA are revealed and further identified using Hirshfeld surface analysis. The utility of the synthons is further demonstrated by making salts with the NA isomer, isonicotinic acid. Here the synthon occurrences in cocrystals/salts of NA (including NA derivatives) and di­amine coformers reported in the Cambridge Structure Database (CSD) are compared. The robustness of acid–ammonium heterodimer and Nammonium—H...Npyridine is investigated by a search of the CSD. The NA salts also show their improved solubility in pH 1.2, 4.5 and 6.8 buffer mediums compared with pure NA material.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619000477/aw5017sup1.cif
Contains datablocks global, DPEN1-NA2, DPEN1-NA2-EA1, DPEN1-NA2-ACN1, DPEN1-INA2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000477/aw5017DPEN1-NA2sup2.hkl
Contains datablock DPEN1-NA2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000477/aw5017DPEN1-NA2-EA1sup3.hkl
Contains datablock DPEN1-NA2-EA1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000477/aw5017DPEN1-NA2-ACN1sup4.hkl
Contains datablock DPEN1-NA2-ACN1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619000477/aw5017DPEN1-INA2sup5.hkl
Contains datablock DPEN1-INA2

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619000477/aw5017sup6.pdf
Figs. S1 to S14, Tables S1 to S3

CCDC references: 1858712; 1858713; 1858714; 1858715

Computing details top

Data collection: SAINT v8.37A (Bruker, 2015) for DPEN1-NA2. Cell refinement: SAINT v8.37A (Bruker, 2015) for DPEN1-NA2, DPEN1-NA2-EA1, DPEN1-NA2-ACN1. Data reduction: SAINT v8.37A (Bruker, 2015) for DPEN1-NA2, DPEN1-NA2-EA1, DPEN1-NA2-ACN1. Program(s) used to solve structure: ShelXT (Sheldrick, 2015) for DPEN1-NA2, DPEN1-NA2-ACN1; SIR2004 (Burla et al., 2007) for DPEN1-INA2. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(DPEN1-NA2) top
Crystal data top
2(C6H4NO2)·2(C7H9N)F(000) = 968
Mr = 458.51Dx = 1.164 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 23.479 (6) ÅCell parameters from 4568 reflections
b = 8.602 (2) Åθ = 3.4–28.0°
c = 16.899 (4) ŵ = 0.08 mm1
β = 129.963 (5)°T = 273 K
V = 2616.1 (11) Å3Plate, colourless
Z = 40.22 × 0.16 × 0.1 mm
Data collection top
CCD area detector
diffractometer
Rint = 0.025
Absorption correction: multi-scan
SADABS 2014/5
θmax = 28.4°, θmin = 3.4°
Tmin = 0.714, Tmax = 0.746h = 3123
11704 measured reflectionsk = 1111
6271 independent reflectionsl = 2122
4303 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.060 w = 1/[σ2(Fo2) + (0.0962P)2 + 0.3861P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.174(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.33 e Å3
6271 reflectionsΔρmin = 0.22 e Å3
368 parametersAbsolute structure: Flack x determined using 1504 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
37 restraintsAbsolute structure parameter: 0.3 (5)
Primary atom site location: dual
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O20.36006 (14)0.4151 (3)0.0583 (2)0.0592 (7)
N10.06036 (16)0.7985 (3)0.1075 (2)0.0395 (6)
O10.46387 (13)0.4848 (4)0.0964 (2)0.0702 (8)
N30.34655 (16)0.6881 (4)0.1734 (2)0.0519 (7)
O40.55418 (17)0.5908 (4)0.4008 (2)0.0740 (8)
N20.5567 (2)0.6958 (4)0.6083 (2)0.0491 (7)
C240.34984 (17)0.5704 (4)0.0475 (3)0.0426 (7)
C250.38318 (17)0.6193 (4)0.1460 (2)0.0443 (7)
H250.4340750.6039580.1969010.053*
O30.6230 (2)0.5019 (5)0.5614 (2)0.0989 (12)
C260.39509 (18)0.4843 (4)0.0268 (3)0.0444 (7)
C10.02056 (17)0.6499 (4)0.0586 (2)0.0428 (7)
H10.0166510.6381750.0673260.051*
C20.0730 (2)0.5128 (4)0.1101 (3)0.0529 (9)
C230.2745 (2)0.5946 (5)0.0285 (3)0.0594 (10)
H230.2500020.5620700.0958680.071*
N40.6549 (6)0.3071 (12)0.3295 (8)0.056 (2)0.697 (9)
C19B0.613 (2)0.359 (4)0.355 (3)0.0446 (19)0.303 (9)
H19B0.5814000.4369490.3102470.054*0.303 (9)
C90.5470 (2)0.9809 (5)0.6180 (3)0.0626 (10)
C210.2736 (2)0.7098 (5)0.0978 (3)0.0608 (10)
H210.2466320.7558950.1144570.073*
C80.5396 (2)0.8471 (4)0.5534 (3)0.0541 (8)
H80.5755320.8628260.5425850.065*
C220.2365 (2)0.6679 (6)0.0025 (3)0.0718 (12)
H220.1860580.6886480.0527250.086*
C200.6035 (2)0.5057 (5)0.4732 (3)0.0582 (9)
C100.5144 (3)0.9734 (5)0.6628 (3)0.0783 (13)
H100.4893490.8835370.6552690.094*
C70.1394 (2)0.5136 (6)0.1291 (4)0.0760 (12)
H70.1534930.6020580.1137540.091*
C50.1658 (4)0.2554 (8)0.1931 (4)0.114 (2)
H50.1970470.1692150.2210180.136*
C180.6457 (5)0.4124 (8)0.4513 (6)0.0442 (14)0.697 (9)
C140.5840 (3)1.1139 (6)0.6308 (4)0.0904 (16)
H140.6070811.1223770.6023660.108*
C130.5867 (4)1.2392 (7)0.6881 (5)0.113 (2)
H130.6117211.3297570.6964390.136*
C120.5549 (4)1.2304 (8)0.7294 (4)0.114 (3)
H120.5570231.3142640.7660010.137*
C30.0529 (3)0.3806 (6)0.1334 (4)0.0831 (14)
H30.0085440.3769110.1218880.100*
C110.5182 (4)1.0963 (7)0.7184 (4)0.105 (2)
H110.4961561.0887450.7482770.126*
C40.1012 (5)0.2513 (6)0.1750 (4)0.109 (2)
H40.0879040.1613550.1903440.131*
C60.1855 (3)0.3859 (8)0.1702 (5)0.1039 (19)
H60.2301940.3888280.1825420.125*
C170.7090 (6)0.3336 (10)0.5287 (5)0.082 (3)0.697 (9)
H170.7270660.3408330.5962310.099*0.697 (9)
C150.7153 (5)0.2325 (11)0.4041 (5)0.087 (3)0.697 (9)
H150.7388240.1695340.3879730.105*0.697 (9)
C160.7456 (6)0.2443 (13)0.5068 (6)0.106 (3)0.697 (9)
H160.7894260.1930720.5589210.127*0.697 (9)
H1A0.029 (2)0.865 (4)0.095 (3)0.039 (9)*
H2A0.593 (2)0.709 (5)0.684 (3)0.054 (10)*
H1B0.095 (2)0.796 (5)0.181 (3)0.053 (10)*
H2B0.569 (2)0.633 (5)0.587 (3)0.056 (11)*
H2C0.513 (3)0.651 (6)0.595 (3)0.076 (14)*
H1C0.090 (2)0.842 (5)0.086 (3)0.061 (11)*
N4A0.6332 (14)0.256 (3)0.317 (2)0.075 (7)0.303 (9)
C16A0.6984 (12)0.138 (3)0.4858 (13)0.106 (3)0.303 (9)
H16A0.7298390.0597470.5312430.127*0.303 (9)
C17A0.6776 (10)0.254 (3)0.5184 (14)0.075 (5)0.303 (9)
H17A0.6940520.2560270.5852090.089*0.303 (9)
C18A0.6330 (13)0.365 (2)0.4502 (17)0.0442 (14)0.303 (9)
C15A0.6727 (13)0.138 (3)0.3859 (15)0.100 (6)0.303 (9)
H15A0.6830800.0513850.3641040.120*0.303 (9)
C190.6209 (8)0.3949 (13)0.3519 (11)0.0446 (19)0.697 (9)
H190.5781990.4476670.2984410.054*0.697 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0528 (14)0.0744 (17)0.0612 (15)0.0098 (12)0.0415 (13)0.0195 (13)
N10.0370 (13)0.0497 (17)0.0330 (14)0.0019 (12)0.0230 (12)0.0002 (11)
O10.0453 (13)0.096 (2)0.0649 (16)0.0140 (14)0.0333 (13)0.0145 (16)
N30.0546 (16)0.0577 (18)0.0505 (15)0.0115 (14)0.0370 (14)0.0044 (14)
O40.0850 (19)0.0796 (19)0.0675 (18)0.0266 (17)0.0536 (16)0.0121 (15)
N20.0636 (19)0.0490 (18)0.0390 (16)0.0033 (14)0.0349 (16)0.0009 (13)
C240.0418 (16)0.0439 (17)0.0466 (18)0.0043 (14)0.0304 (15)0.0042 (14)
C250.0373 (15)0.052 (2)0.0412 (17)0.0080 (14)0.0242 (14)0.0015 (14)
O30.128 (3)0.116 (3)0.0622 (18)0.048 (2)0.0659 (19)0.0099 (19)
C260.0459 (17)0.0477 (18)0.0506 (19)0.0007 (14)0.0361 (16)0.0005 (16)
C10.0405 (15)0.0543 (19)0.0359 (15)0.0028 (14)0.0257 (13)0.0018 (14)
C20.057 (2)0.049 (2)0.0370 (17)0.0013 (16)0.0231 (16)0.0008 (15)
C230.0462 (18)0.077 (3)0.0434 (18)0.0069 (18)0.0236 (15)0.0065 (18)
N40.058 (5)0.063 (5)0.037 (4)0.007 (3)0.025 (4)0.006 (3)
C19B0.043 (4)0.047 (6)0.038 (2)0.002 (4)0.023 (2)0.008 (4)
C90.077 (3)0.045 (2)0.0391 (18)0.0009 (18)0.0249 (18)0.0029 (15)
C210.054 (2)0.073 (3)0.067 (2)0.0183 (18)0.0441 (19)0.003 (2)
C80.071 (2)0.049 (2)0.0439 (17)0.0058 (17)0.0374 (17)0.0011 (15)
C220.0394 (18)0.099 (3)0.057 (2)0.018 (2)0.0216 (17)0.002 (2)
C200.065 (2)0.061 (2)0.050 (2)0.004 (2)0.0376 (19)0.0047 (19)
C100.123 (4)0.055 (2)0.059 (2)0.007 (2)0.059 (3)0.002 (2)
C70.066 (2)0.071 (3)0.080 (3)0.019 (2)0.042 (2)0.011 (2)
C50.111 (5)0.064 (3)0.071 (3)0.024 (3)0.015 (3)0.004 (3)
C180.053 (4)0.037 (4)0.0405 (19)0.000 (3)0.029 (2)0.003 (3)
C140.097 (3)0.065 (3)0.068 (3)0.017 (3)0.034 (3)0.003 (2)
C130.115 (5)0.052 (3)0.079 (4)0.005 (3)0.019 (4)0.008 (3)
C120.137 (6)0.072 (4)0.060 (3)0.024 (4)0.030 (3)0.013 (3)
C30.092 (3)0.063 (3)0.059 (3)0.019 (2)0.032 (2)0.005 (2)
C110.151 (5)0.076 (4)0.071 (3)0.027 (4)0.064 (3)0.006 (3)
C40.138 (5)0.046 (3)0.070 (3)0.009 (3)0.034 (4)0.010 (2)
C60.085 (3)0.088 (4)0.100 (4)0.031 (3)0.042 (3)0.004 (3)
C170.111 (6)0.076 (5)0.037 (3)0.039 (4)0.037 (4)0.010 (3)
C150.097 (5)0.101 (6)0.052 (3)0.052 (5)0.042 (4)0.007 (4)
C160.108 (5)0.119 (6)0.057 (3)0.068 (4)0.038 (4)0.011 (4)
N4A0.065 (14)0.089 (18)0.036 (7)0.028 (10)0.016 (9)0.009 (10)
C16A0.108 (5)0.119 (6)0.057 (3)0.068 (4)0.038 (4)0.011 (4)
C17A0.071 (8)0.097 (11)0.067 (8)0.035 (7)0.049 (7)0.013 (8)
C18A0.053 (4)0.037 (4)0.0405 (19)0.000 (3)0.029 (2)0.003 (3)
C15A0.109 (11)0.105 (11)0.080 (9)0.038 (9)0.058 (8)0.007 (8)
C190.043 (4)0.047 (6)0.038 (2)0.002 (4)0.023 (2)0.008 (4)
Geometric parameters (Å, º) top
O2—C261.257 (4)C22—H220.9300
N1—C11.482 (4)C20—C181.492 (9)
N1—H1A0.85 (4)C20—C18A1.56 (2)
N1—H1B0.95 (4)C10—H100.9300
N1—H1C1.04 (4)C10—C111.378 (7)
O1—C261.246 (4)C7—H70.9300
N3—C251.347 (4)C7—C61.376 (7)
N3—C211.338 (5)C5—H50.9300
O4—C201.246 (5)C5—C41.344 (10)
N2—C81.496 (5)C5—C61.361 (11)
N2—H2A0.99 (4)C18—C171.371 (11)
N2—H2B0.80 (5)C18—C191.389 (17)
N2—H2C0.97 (5)C14—H140.9300
C24—C251.374 (5)C14—C131.422 (9)
C24—C261.509 (4)C13—H130.9300
C24—C231.379 (5)C13—C121.314 (11)
C25—H250.9300C12—H120.9300
O3—C201.248 (5)C12—C111.378 (10)
C1—C1i1.549 (6)C3—H30.9300
C1—H10.9800C3—C41.411 (9)
C1—C21.513 (5)C11—H110.9300
C2—C71.375 (6)C4—H40.9300
C2—C31.383 (6)C6—H60.9300
C23—H230.9300C17—H170.9300
C23—C221.375 (6)C17—C161.370 (11)
N4—C151.310 (13)C15—H150.9300
N4—C191.32 (2)C15—C161.394 (10)
C19B—H19B0.9300C16—H160.9300
C19B—N4A1.34 (5)N4A—C15A1.36 (4)
C19B—C18A1.35 (5)C16A—H16A0.9300
C9—C81.517 (6)C16A—C17A1.37 (2)
C9—C101.380 (7)C16A—C15A1.38 (3)
C9—C141.367 (7)C17A—H17A0.9300
C21—H210.9300C17A—C18A1.33 (3)
C21—C221.366 (6)C15A—H15A0.9300
C8—C8ii1.551 (8)C19—H190.9300
C8—H80.9800
C1—N1—H1A107 (2)C9—C10—H10119.3
C1—N1—H1B114 (2)C11—C10—C9121.5 (5)
C1—N1—H1C116 (2)C11—C10—H10119.3
H1A—N1—H1B103 (3)C2—C7—H7119.4
H1A—N1—H1C110 (3)C2—C7—C6121.3 (5)
H1B—N1—H1C105 (3)C6—C7—H7119.4
C21—N3—C25116.2 (3)C4—C5—H5120.1
C8—N2—H2A112 (2)C4—C5—C6119.8 (5)
C8—N2—H2B110 (3)C6—C5—H5120.1
C8—N2—H2C112 (3)C17—C18—C20121.0 (7)
H2A—N2—H2B114 (4)C17—C18—C19117.0 (9)
H2A—N2—H2C104 (3)C19—C18—C20121.9 (9)
H2B—N2—H2C105 (4)C9—C14—H14120.4
C25—C24—C26119.6 (3)C9—C14—C13119.3 (6)
C25—C24—C23118.3 (3)C13—C14—H14120.4
C23—C24—C26122.0 (3)C14—C13—H13119.1
N3—C25—C24123.9 (3)C12—C13—C14121.7 (6)
N3—C25—H25118.0C12—C13—H13119.1
C24—C25—H25118.0C13—C12—H12120.2
O2—C26—C24117.2 (3)C13—C12—C11119.7 (6)
O1—C26—O2125.5 (3)C11—C12—H12120.2
O1—C26—C24117.3 (3)C2—C3—H3120.7
N1—C1—C1i111.42 (18)C2—C3—C4118.7 (6)
N1—C1—H1108.0C4—C3—H3120.7
N1—C1—C2111.2 (2)C10—C11—H11120.1
C1i—C1—H1108.0C12—C11—C10119.7 (6)
C2—C1—C1i110.1 (2)C12—C11—H11120.1
C2—C1—H1108.0C5—C4—C3121.3 (6)
C7—C2—C1120.9 (4)C5—C4—H4119.3
C7—C2—C3118.7 (4)C3—C4—H4119.3
C3—C2—C1120.3 (4)C7—C6—H6119.9
C24—C23—H23120.7C5—C6—C7120.2 (6)
C22—C23—C24118.6 (3)C5—C6—H6119.9
C22—C23—H23120.7C18—C17—H17119.9
C15—N4—C19119.0 (11)C16—C17—C18120.3 (7)
N4A—C19B—H19B115.3C16—C17—H17119.9
N4A—C19B—C18A129 (3)N4—C15—H15118.9
C18A—C19B—H19B115.3N4—C15—C16122.2 (8)
C10—C9—C8120.8 (4)C16—C15—H15118.9
C14—C9—C8121.1 (4)C17—C16—C15118.1 (6)
C14—C9—C10118.1 (4)C17—C16—H16121.0
N3—C21—H21118.3C15—C16—H16121.0
N3—C21—C22123.5 (3)C19B—N4A—C15A110 (3)
C22—C21—H21118.3C17A—C16A—H16A119.8
N2—C8—C9110.7 (3)C17A—C16A—C15A120.3 (17)
N2—C8—C8ii111.4 (2)C15A—C16A—H16A119.8
N2—C8—H8108.4C16A—C17A—H17A121.4
C9—C8—C8ii109.5 (3)C18A—C17A—C16A117.1 (17)
C9—C8—H8108.4C18A—C17A—H17A121.4
C8ii—C8—H8108.4C19B—C18A—C20117 (2)
C23—C22—H22120.3C17A—C18A—C19B119 (2)
C21—C22—C23119.4 (3)C17A—C18A—C20124.4 (18)
C21—C22—H22120.3N4A—C15A—C16A124 (2)
O4—C20—O3125.7 (4)N4A—C15A—H15A117.9
O4—C20—C18114.8 (4)C16A—C15A—H15A117.9
O4—C20—C18A119.5 (9)N4—C19—C18123.3 (12)
O3—C20—C18119.3 (5)N4—C19—H19118.3
O3—C20—C18A113.3 (9)C18—C19—H19118.3
N1—C1—C2—C748.1 (4)C9—C14—C13—C120.3 (9)
N1—C1—C2—C3135.7 (4)C21—N3—C25—C240.8 (5)
N3—C21—C22—C232.3 (8)C8—C9—C10—C11177.5 (4)
O4—C20—C18—C17169.3 (7)C8—C9—C14—C13177.2 (4)
O4—C20—C18—C1913.9 (8)C20—C18—C17—C16177.8 (9)
O4—C20—C18A—C19B12 (2)C20—C18—C19—N4176.6 (7)
O4—C20—C18A—C17A170.3 (16)C10—C9—C8—N247.9 (5)
C24—C23—C22—C212.1 (7)C10—C9—C8—C8ii75.3 (5)
C25—N3—C21—C220.8 (6)C10—C9—C14—C130.8 (7)
C25—C24—C26—O2166.1 (3)C7—C2—C3—C40.5 (7)
C25—C24—C26—O112.3 (5)C18—C17—C16—C152.0 (17)
C25—C24—C23—C220.7 (6)C14—C9—C8—N2134.1 (4)
O3—C20—C18—C175.7 (9)C14—C9—C8—C8ii102.7 (5)
O3—C20—C18—C19171.1 (6)C14—C9—C10—C110.5 (7)
O3—C20—C18A—C19B179.0 (17)C14—C13—C12—C110.6 (10)
O3—C20—C18A—C17A3 (2)C13—C12—C11—C100.9 (9)
C26—C24—C25—N3175.7 (3)C3—C2—C7—C60.1 (7)
C26—C24—C23—C22177.1 (4)C4—C5—C6—C70.1 (10)
C1i—C1—C2—C775.9 (4)C6—C5—C4—C30.5 (10)
C1i—C1—C2—C3100.3 (4)C17—C18—C19—N40.3 (11)
C1—C2—C7—C6176.1 (4)C15—N4—C19—C180.3 (13)
C1—C2—C3—C4175.8 (4)N4A—C19B—C18A—C20177 (2)
C2—C7—C6—C50.0 (9)N4A—C19B—C18A—C17A1 (4)
C2—C3—C4—C50.7 (8)C16A—C17A—C18A—C19B2 (3)
C23—C24—C25—N30.8 (6)C16A—C17A—C18A—C20180.0 (19)
C23—C24—C26—O210.2 (5)C17A—C16A—C15A—N4A7 (4)
C23—C24—C26—O1171.4 (4)C18A—C19B—N4A—C15A7 (4)
N4—C15—C16—C172.1 (18)C15A—C16A—C17A—C18A1 (4)
C19B—N4A—C15A—C16A10 (4)C19—N4—C15—C160.9 (16)
C9—C10—C11—C120.4 (8)C19—C18—C17—C160.9 (14)
Symmetry codes: (i) x, y, z; (ii) x+1, y, z+1.
(DPEN1-NA2-EA1) top
Crystal data top
2(C6H4NO2)·2(C7H9N)·C4H8O2F(000) = 1160
Mr = 546.61Dx = 1.211 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71076 Å
a = 22.9673 (11) ÅCell parameters from 9833 reflections
b = 8.8676 (4) Åθ = 3.1–28.3°
c = 16.7749 (8) ŵ = 0.09 mm1
β = 118.613 (2)°T = 273 K
V = 2999.2 (2) Å3Needle, colourless
Z = 40.23 × 0.17 × 0.09 mm
Data collection top
CCD area detector
diffractometer
θmax = 28.3°, θmin = 3.1°
25955 measured reflectionsh = 3030
7385 independent reflectionsk = 1111
6427 reflections with I > 2σ(I)l = 2222
Rint = 0.023
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.052 w = 1/[σ2(Fo2) + (0.0861P)2 + 0.8946P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.152(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.55 e Å3
7385 reflectionsΔρmin = 0.35 e Å3
387 parametersAbsolute structure: Flack x determined using 2721 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraintAbsolute structure parameter: 0.27 (18)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O40.54861 (12)0.4041 (3)0.18285 (15)0.0606 (5)
O10.46407 (11)0.5224 (3)0.34732 (15)0.0642 (6)
O30.59492 (11)0.5086 (3)0.10566 (14)0.0611 (5)
O20.37176 (12)0.5937 (3)0.34938 (16)0.0703 (7)
N20.45082 (11)0.2941 (3)0.02723 (14)0.0406 (4)
N10.55293 (12)0.6970 (3)0.47865 (15)0.0430 (5)
N30.35886 (12)0.3121 (3)0.09945 (16)0.0548 (6)
N40.62868 (13)0.7213 (3)0.38490 (16)0.0543 (6)
C140.51476 (12)0.8387 (3)0.46704 (15)0.0408 (5)
H140.47790.84110.40480.049*
C70.46490 (10)0.1472 (3)0.00403 (14)0.0365 (5)
H70.43210.13230.06790.044*
C250.60351 (14)0.6194 (3)0.31861 (18)0.0466 (5)
H250.57530.54640.32090.056*
C200.40245 (14)0.5266 (3)0.31496 (17)0.0469 (5)
C60.45964 (11)0.0172 (3)0.05089 (16)0.0390 (5)
C240.61697 (12)0.6156 (3)0.24625 (16)0.0403 (5)
C50.48820 (15)0.0263 (4)0.14490 (18)0.0510 (6)
H50.50920.11480.17450.061*
C190.39182 (12)0.3822 (3)0.17957 (18)0.0463 (6)
H190.43780.38760.20580.056*
O50.24709 (16)0.8768 (4)0.2538 (2)0.0899 (9)
C180.36205 (13)0.4471 (3)0.22577 (17)0.0438 (5)
C260.58409 (13)0.4997 (3)0.17210 (17)0.0457 (5)
C130.55717 (14)0.9772 (3)0.48090 (19)0.0473 (6)
C150.29348 (16)0.3055 (5)0.0632 (2)0.0670 (9)
H150.26970.25570.00810.080*
C120.53189 (18)1.0991 (4)0.4225 (3)0.0660 (8)
H120.48951.09450.37300.079*
C170.29360 (16)0.4399 (5)0.1857 (2)0.0647 (9)
H170.27120.48250.21390.078*
C10.42890 (15)0.1152 (4)0.0083 (2)0.0558 (7)
H10.40960.12270.05460.067*
O60.18450 (18)0.6719 (5)0.1952 (3)0.1238 (16)
C230.65908 (15)0.7241 (3)0.2441 (2)0.0511 (6)
H230.66920.72610.19670.061*
C40.4855 (2)0.0956 (4)0.1946 (2)0.0669 (9)
H40.50520.08900.25750.080*
C210.66925 (17)0.8255 (4)0.3812 (2)0.0599 (7)
H210.68680.89800.42680.072*
C80.62067 (16)0.9859 (4)0.5537 (2)0.0623 (8)
H80.63800.90490.59350.075*
C110.5700 (3)1.2277 (5)0.4381 (4)0.0922 (14)
H110.55291.31000.39930.111*
C160.25914 (16)0.3682 (6)0.1029 (3)0.0784 (12)
H160.21310.36260.07440.094*
C220.68621 (19)0.8301 (4)0.3129 (2)0.0621 (8)
H220.71530.90310.31300.074*
C30.4540 (2)0.2268 (4)0.1515 (3)0.0696 (9)
H30.45120.30730.18500.084*
C100.6323 (3)1.2345 (5)0.5097 (4)0.0994 (16)
H100.65751.32140.51960.119*
C20.42661 (18)0.2378 (4)0.0587 (3)0.0703 (9)
H20.40650.32720.02950.084*
C90.6583 (2)1.1138 (5)0.5675 (3)0.0871 (12)
H90.70121.11860.61580.105*
C290.2110 (2)0.7601 (6)0.2574 (4)0.0903 (14)
C300.2089 (3)0.7562 (7)0.3430 (5)0.1121 (18)
H30A0.25060.72050.39050.168*
H30B0.17410.68970.33720.168*
H30C0.20050.85580.35760.168*
C280.2540 (3)0.8910 (13)0.1735 (4)0.145 (3)
H28A0.24720.79300.14470.174*
H28B0.21990.95830.13120.174*
C270.3163 (4)0.9466 (14)0.1914 (6)0.162 (4)
H27A0.32020.94270.13700.243*
H27B0.35050.88600.23750.243*
H27C0.32091.04900.21210.243*
H2A0.4351 (15)0.368 (4)0.024 (2)0.046 (8)*
H1A0.5765 (18)0.714 (4)0.455 (2)0.052 (8)*
H1B0.5791 (15)0.661 (4)0.538 (2)0.042 (7)*
H2B0.4195 (19)0.282 (4)0.043 (2)0.059 (9)*
H1C0.523 (2)0.622 (5)0.444 (3)0.061 (10)*
H2C0.490 (2)0.331 (5)0.085 (3)0.075 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0688 (13)0.0592 (12)0.0578 (11)0.0176 (10)0.0333 (10)0.0136 (10)
O10.0528 (11)0.0734 (14)0.0601 (12)0.0070 (11)0.0220 (9)0.0216 (11)
O30.0729 (13)0.0692 (14)0.0512 (10)0.0082 (11)0.0378 (10)0.0121 (10)
O20.0702 (14)0.0864 (17)0.0565 (12)0.0071 (12)0.0321 (11)0.0224 (12)
N20.0413 (10)0.0492 (12)0.0428 (10)0.0042 (8)0.0294 (9)0.0036 (9)
N10.0464 (11)0.0498 (12)0.0409 (10)0.0021 (9)0.0275 (9)0.0011 (9)
N30.0513 (12)0.0741 (17)0.0505 (12)0.0074 (11)0.0337 (10)0.0131 (11)
N40.0638 (14)0.0602 (14)0.0512 (12)0.0083 (12)0.0373 (11)0.0080 (11)
C140.0425 (11)0.0474 (13)0.0330 (10)0.0007 (10)0.0183 (9)0.0026 (9)
C70.0317 (10)0.0485 (13)0.0318 (9)0.0003 (9)0.0174 (8)0.0023 (9)
C250.0510 (13)0.0471 (13)0.0511 (13)0.0050 (11)0.0319 (11)0.0001 (11)
C200.0549 (14)0.0444 (13)0.0444 (12)0.0002 (11)0.0263 (11)0.0041 (10)
C60.0344 (10)0.0461 (12)0.0418 (11)0.0002 (9)0.0226 (9)0.0001 (10)
C240.0413 (11)0.0410 (12)0.0412 (11)0.0033 (9)0.0219 (9)0.0020 (9)
C50.0631 (15)0.0524 (15)0.0420 (12)0.0008 (13)0.0288 (11)0.0032 (11)
C190.0405 (11)0.0573 (15)0.0489 (13)0.0042 (11)0.0276 (10)0.0074 (11)
O50.0809 (17)0.108 (2)0.0699 (16)0.0042 (18)0.0271 (13)0.0195 (16)
C180.0441 (12)0.0482 (13)0.0449 (12)0.0013 (10)0.0260 (10)0.0022 (10)
C260.0458 (12)0.0481 (14)0.0444 (12)0.0035 (11)0.0225 (10)0.0029 (10)
C130.0516 (13)0.0490 (14)0.0469 (13)0.0002 (11)0.0282 (11)0.0046 (11)
C150.0562 (16)0.098 (3)0.0490 (14)0.0160 (17)0.0270 (13)0.0205 (16)
C120.0634 (18)0.0617 (18)0.073 (2)0.0058 (15)0.0325 (16)0.0179 (16)
C170.0488 (15)0.092 (2)0.0655 (18)0.0001 (15)0.0370 (14)0.0173 (17)
C10.0471 (13)0.0615 (17)0.0616 (16)0.0116 (12)0.0284 (12)0.0122 (14)
O60.078 (2)0.110 (3)0.142 (3)0.0076 (19)0.020 (2)0.049 (3)
C230.0620 (16)0.0517 (15)0.0546 (14)0.0001 (12)0.0401 (13)0.0032 (12)
C40.083 (2)0.070 (2)0.0585 (17)0.0135 (18)0.0425 (17)0.0195 (16)
C210.0733 (19)0.0537 (16)0.0619 (16)0.0144 (14)0.0398 (15)0.0157 (14)
C80.0565 (16)0.0574 (18)0.0618 (17)0.0095 (14)0.0194 (14)0.0050 (14)
C110.103 (3)0.054 (2)0.127 (4)0.005 (2)0.061 (3)0.033 (2)
C160.0409 (14)0.126 (4)0.0682 (19)0.0060 (19)0.0259 (14)0.022 (2)
C220.078 (2)0.0504 (16)0.0760 (19)0.0186 (15)0.0519 (17)0.0089 (15)
C30.075 (2)0.0544 (17)0.095 (3)0.0074 (16)0.054 (2)0.0207 (18)
C100.090 (3)0.063 (2)0.140 (4)0.024 (2)0.050 (3)0.001 (3)
C20.0625 (18)0.0484 (16)0.108 (3)0.0109 (14)0.048 (2)0.0080 (18)
C90.068 (2)0.076 (3)0.096 (3)0.022 (2)0.022 (2)0.001 (2)
C290.058 (2)0.081 (3)0.103 (3)0.018 (2)0.015 (2)0.026 (2)
C300.128 (5)0.081 (3)0.137 (5)0.012 (3)0.071 (4)0.014 (3)
C280.111 (4)0.248 (10)0.079 (3)0.009 (6)0.048 (3)0.023 (5)
C270.127 (5)0.223 (10)0.141 (6)0.006 (6)0.067 (5)0.058 (7)
Geometric parameters (Å, º) top
O4—C261.247 (4)C15—H150.9300
O1—C201.250 (3)C15—C161.370 (5)
O3—C261.255 (3)C12—H120.9300
O2—C201.254 (3)C12—C111.384 (6)
N2—C71.496 (3)C17—H170.9300
N2—H2A1.00 (3)C17—C161.380 (5)
N2—H2B0.88 (4)C1—H10.9300
N2—H2C1.01 (4)C1—C21.393 (5)
N1—C141.491 (3)O6—C291.209 (6)
N1—H1A0.82 (4)C23—H230.9300
N1—H1B0.95 (3)C23—C221.384 (4)
N1—H1C0.94 (4)C4—H40.9300
N3—C191.338 (4)C4—C31.377 (6)
N3—C151.324 (4)C21—H210.9300
N4—C251.331 (4)C21—C221.376 (4)
N4—C211.335 (4)C8—H80.9300
C14—C14i1.549 (4)C8—C91.377 (5)
C14—H140.9800C11—H110.9300
C14—C131.514 (4)C11—C101.359 (8)
C7—C7ii1.552 (4)C16—H160.9300
C7—H70.9800C22—H220.9300
C7—C61.516 (3)C3—H30.9300
C25—H250.9300C3—C21.376 (6)
C25—C241.389 (3)C10—H100.9300
C20—C181.506 (4)C10—C91.373 (7)
C6—C51.390 (3)C2—H20.9300
C6—C11.380 (4)C9—H90.9300
C24—C261.508 (4)C29—C301.461 (8)
C24—C231.377 (4)C30—H30A0.9600
C5—H50.9300C30—H30B0.9600
C5—C41.385 (4)C30—H30C0.9600
C19—H190.9300C28—H28A0.9700
C19—C181.381 (3)C28—H28B0.9700
O5—C291.345 (6)C28—C271.404 (11)
O5—C281.436 (6)C27—H27A0.9600
C18—C171.384 (4)C27—H27B0.9600
C13—C121.385 (4)C27—H27C0.9600
C13—C81.385 (4)
C7—N2—H2A108.6 (19)C18—C17—H17120.6
C7—N2—H2B110 (3)C16—C17—C18118.8 (3)
C7—N2—H2C112 (3)C16—C17—H17120.6
H2A—N2—H2B109 (3)C6—C1—H1119.7
H2A—N2—H2C113 (3)C6—C1—C2120.5 (3)
H2B—N2—H2C104 (3)C2—C1—H1119.7
C14—N1—H1A105 (3)C24—C23—H23120.2
C14—N1—H1B117.5 (19)C24—C23—C22119.6 (2)
C14—N1—H1C108 (2)C22—C23—H23120.2
H1A—N1—H1B110 (3)C5—C4—H4119.7
H1A—N1—H1C107 (3)C3—C4—C5120.5 (3)
H1B—N1—H1C109 (3)C3—C4—H4119.7
C15—N3—C19117.0 (2)N4—C21—H21118.6
C25—N4—C21117.7 (2)N4—C21—C22122.8 (3)
N1—C14—C14i109.73 (14)C22—C21—H21118.6
N1—C14—H14108.1C13—C8—H8119.9
N1—C14—C13111.6 (2)C9—C8—C13120.3 (3)
C14i—C14—H14108.1C9—C8—H8119.9
C13—C14—C14i111.07 (16)C12—C11—H11119.8
C13—C14—H14108.1C10—C11—C12120.4 (4)
N2—C7—C7ii111.06 (14)C10—C11—H11119.8
N2—C7—H7108.6C15—C16—C17119.3 (3)
N2—C7—C6110.81 (18)C15—C16—H16120.4
C7ii—C7—H7108.6C17—C16—H16120.4
C6—C7—C7ii109.19 (16)C23—C22—H22120.7
C6—C7—H7108.6C21—C22—C23118.7 (3)
N4—C25—H25118.1C21—C22—H22120.7
N4—C25—C24123.8 (2)C4—C3—H3120.2
C24—C25—H25118.1C2—C3—C4119.6 (3)
O1—C20—O2125.7 (3)C2—C3—H3120.2
O1—C20—C18116.6 (2)C11—C10—H10119.8
O2—C20—C18117.7 (2)C11—C10—C9120.5 (4)
C5—C6—C7120.9 (2)C9—C10—H10119.8
C1—C6—C7120.1 (2)C1—C2—H2119.9
C1—C6—C5118.9 (3)C3—C2—C1120.1 (3)
C25—C24—C26120.3 (2)C3—C2—H2119.9
C23—C24—C25117.3 (2)C8—C9—H9120.1
C23—C24—C26122.4 (2)C10—C9—C8119.9 (4)
C6—C5—H5119.9C10—C9—H9120.1
C4—C5—C6120.3 (3)O5—C29—C30111.9 (4)
C4—C5—H5119.9O6—C29—O5121.7 (6)
N3—C19—H19117.9O6—C29—C30126.4 (6)
N3—C19—C18124.3 (2)C29—C30—H30A109.5
C18—C19—H19117.9C29—C30—H30B109.5
C29—O5—C28117.2 (5)C29—C30—H30C109.5
C19—C18—C20121.2 (2)H30A—C30—H30B109.5
C19—C18—C17117.4 (2)H30A—C30—H30C109.5
C17—C18—C20121.4 (2)H30B—C30—H30C109.5
O4—C26—O3126.3 (3)O5—C28—H28A109.0
O4—C26—C24116.6 (2)O5—C28—H28B109.0
O3—C26—C24117.1 (2)H28A—C28—H28B107.8
C12—C13—C14120.2 (3)C27—C28—O5112.9 (6)
C8—C13—C14120.6 (3)C27—C28—H28A109.0
C8—C13—C12119.2 (3)C27—C28—H28B109.0
N3—C15—H15118.3C28—C27—H27A109.5
N3—C15—C16123.3 (3)C28—C27—H27B109.5
C16—C15—H15118.3C28—C27—H27C109.5
C13—C12—H12120.1H27A—C27—H27B109.5
C11—C12—C13119.8 (4)H27A—C27—H27C109.5
C11—C12—H12120.1H27B—C27—H27C109.5
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z.
(DPEN1-NA2-ACN1) top
Crystal data top
2(C6H4NO2)·C14H18N2·C2H3NDx = 1.213 Mg m3
Mr = 499.56Mo Kα radiation, λ = 0.71076 Å
Orthorhombic, P212121Cell parameters from 6368 reflections
a = 11.770 (8) Åθ = 3.0–28.3°
b = 14.079 (10) ŵ = 0.08 mm1
c = 16.502 (12) ÅT = 273 K
V = 2734 (3) Å3Plate, colourless
Z = 40.16 × 0.14 × 0.11 mm
F(000) = 1056
Data collection top
CCD area detector
diffractometer
θmax = 28.5°, θmin = 2.9°
50039 measured reflectionsh = 1515
6822 independent reflectionsk = 1818
5953 reflections with I > 2σ(I)l = 2222
Rint = 0.033
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0562P)2 + 0.3294P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.18 e Å3
6822 reflectionsΔρmin = 0.15 e Å3
359 parametersAbsolute structure: Flack x determined using 2398 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraintsAbsolute structure parameter: 0.3 (2)
Primary atom site location: dual
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O40.64925 (16)0.33234 (12)0.53942 (10)0.0618 (4)
N10.40239 (13)0.47996 (11)0.60982 (9)0.0324 (3)
O20.36217 (14)0.66424 (11)0.55123 (10)0.0550 (4)
O30.48724 (15)0.38030 (12)0.48295 (10)0.0583 (4)
N20.63956 (13)0.50560 (12)0.60726 (9)0.0346 (3)
N40.69423 (15)0.12510 (12)0.36712 (11)0.0461 (4)
O10.55086 (16)0.65893 (14)0.53993 (13)0.0743 (6)
N30.35530 (15)0.90372 (14)0.40284 (14)0.0575 (5)
C190.67551 (17)0.19076 (13)0.42384 (12)0.0414 (4)
H190.72240.19120.46920.050*
C200.57422 (18)0.32924 (14)0.48634 (12)0.0432 (4)
C260.45537 (18)0.69471 (14)0.52644 (11)0.0419 (4)
C90.66486 (14)0.47029 (13)0.75030 (11)0.0346 (4)
C180.59025 (16)0.25829 (13)0.41911 (12)0.0389 (4)
C240.45687 (16)0.78237 (13)0.47390 (11)0.0374 (4)
C80.58324 (13)0.50966 (12)0.68766 (10)0.0309 (3)
H80.56970.57660.70070.037*
C70.46710 (14)0.45902 (12)0.68598 (10)0.0315 (3)
H70.48120.39050.68780.038*
C250.35733 (17)0.82754 (15)0.45106 (13)0.0456 (5)
H250.28870.80370.47020.055*
C60.39406 (15)0.48467 (16)0.75875 (11)0.0404 (4)
C150.6282 (2)0.12765 (17)0.30187 (15)0.0540 (5)
H150.64060.08290.26140.065*
C230.55903 (17)0.81906 (15)0.44570 (14)0.0488 (5)
H230.62750.79100.46050.059*
C10.3506 (2)0.57543 (19)0.76651 (16)0.0574 (6)
H10.36890.62180.72850.069*
C100.74631 (18)0.52982 (15)0.78345 (13)0.0473 (5)
H100.74730.59360.76880.057*
C170.5228 (2)0.25882 (18)0.35092 (15)0.0584 (6)
H170.46470.30310.34550.070*
C220.5582 (2)0.89685 (19)0.39597 (18)0.0637 (7)
H220.62560.92210.37600.076*
C140.6659 (2)0.37565 (17)0.77302 (16)0.0580 (6)
H140.61350.33360.75080.070*
N50.5680 (3)0.7209 (2)0.8327 (3)0.1104 (12)
C210.4548 (2)0.93689 (18)0.37629 (18)0.0652 (7)
H210.45450.98990.34270.078*
C120.8243 (2)0.4030 (2)0.86100 (15)0.0627 (6)
H120.87670.38050.89850.075*
C110.8264 (2)0.4961 (2)0.83805 (14)0.0599 (6)
H110.88130.53680.85890.072*
C50.3668 (2)0.4173 (2)0.81580 (14)0.0608 (6)
H50.39570.35600.81160.073*
C280.5718 (3)0.6687 (3)0.8850 (3)0.0829 (10)
C160.5425 (2)0.1928 (2)0.29087 (16)0.0681 (7)
H160.49880.19240.24390.082*
C130.7453 (2)0.3433 (2)0.82899 (19)0.0716 (8)
H130.74440.27990.84480.086*
C40.2951 (3)0.4417 (3)0.88055 (17)0.0875 (11)
H40.27690.39640.91950.105*
C20.2793 (3)0.5974 (3)0.8314 (2)0.0853 (10)
H20.25060.65870.83630.102*
C30.2516 (3)0.5317 (4)0.88688 (19)0.0939 (12)
H30.20300.54710.92940.113*
C270.5764 (4)0.6001 (3)0.9494 (3)0.1070 (13)
H27A0.60630.54140.92900.161*
H27B0.50130.58980.97030.161*
H27C0.62460.62340.99190.161*
H1A0.395 (2)0.5417 (18)0.5997 (14)0.043 (6)*
H1B0.4397 (19)0.4490 (16)0.5677 (14)0.040 (5)*
H1C0.334 (2)0.4522 (17)0.6156 (14)0.046 (6)*
H2A0.645 (2)0.446 (2)0.5853 (17)0.061 (7)*
H2B0.710 (2)0.5282 (18)0.6092 (14)0.050 (6)*
H2C0.605 (2)0.5452 (17)0.5731 (15)0.046 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0726 (11)0.0595 (10)0.0534 (9)0.0190 (8)0.0116 (8)0.0151 (7)
N10.0282 (6)0.0349 (8)0.0342 (7)0.0010 (6)0.0017 (6)0.0017 (6)
O20.0555 (9)0.0461 (8)0.0634 (9)0.0062 (7)0.0115 (8)0.0161 (7)
O30.0625 (9)0.0610 (9)0.0515 (8)0.0241 (8)0.0004 (7)0.0128 (7)
N20.0265 (6)0.0382 (8)0.0389 (8)0.0005 (6)0.0020 (6)0.0094 (6)
N40.0416 (9)0.0397 (8)0.0571 (10)0.0071 (7)0.0026 (8)0.0055 (7)
O10.0578 (10)0.0721 (11)0.0929 (13)0.0241 (9)0.0051 (10)0.0417 (10)
N30.0359 (8)0.0586 (11)0.0780 (13)0.0083 (8)0.0010 (9)0.0311 (10)
C190.0401 (9)0.0405 (9)0.0437 (10)0.0033 (8)0.0010 (8)0.0014 (8)
C200.0525 (11)0.0384 (9)0.0386 (9)0.0064 (8)0.0064 (8)0.0007 (7)
C260.0487 (10)0.0386 (9)0.0385 (9)0.0113 (8)0.0029 (8)0.0051 (7)
C90.0314 (8)0.0377 (9)0.0345 (8)0.0008 (7)0.0001 (7)0.0009 (7)
C180.0391 (9)0.0360 (9)0.0417 (9)0.0029 (7)0.0033 (8)0.0002 (7)
C240.0372 (8)0.0353 (8)0.0396 (9)0.0062 (7)0.0004 (8)0.0021 (7)
C80.0291 (7)0.0264 (7)0.0373 (8)0.0005 (6)0.0007 (6)0.0002 (6)
C70.0299 (7)0.0303 (7)0.0342 (8)0.0018 (6)0.0019 (7)0.0019 (6)
C250.0326 (9)0.0479 (11)0.0562 (11)0.0029 (8)0.0025 (8)0.0166 (9)
C60.0301 (8)0.0571 (11)0.0340 (8)0.0049 (8)0.0024 (7)0.0032 (8)
C150.0496 (11)0.0537 (12)0.0587 (13)0.0050 (10)0.0012 (10)0.0194 (10)
C230.0328 (9)0.0469 (11)0.0665 (13)0.0069 (8)0.0018 (9)0.0088 (9)
C10.0491 (12)0.0626 (14)0.0604 (14)0.0057 (10)0.0116 (10)0.0149 (11)
C100.0504 (11)0.0425 (10)0.0489 (11)0.0014 (9)0.0081 (9)0.0086 (9)
C170.0528 (13)0.0584 (13)0.0641 (13)0.0219 (11)0.0149 (11)0.0122 (11)
C220.0374 (10)0.0607 (14)0.0930 (19)0.0037 (10)0.0069 (11)0.0266 (13)
C140.0522 (12)0.0449 (11)0.0769 (15)0.0076 (9)0.0218 (11)0.0174 (11)
N50.109 (2)0.0587 (16)0.164 (3)0.0135 (16)0.015 (2)0.012 (2)
C210.0448 (11)0.0590 (14)0.0916 (18)0.0026 (10)0.0031 (13)0.0397 (13)
C120.0577 (14)0.0825 (17)0.0477 (12)0.0078 (12)0.0159 (11)0.0095 (12)
C110.0549 (12)0.0704 (15)0.0545 (12)0.0024 (12)0.0179 (10)0.0189 (11)
C50.0525 (12)0.0850 (17)0.0448 (11)0.0081 (12)0.0064 (10)0.0140 (12)
C280.0654 (18)0.0644 (18)0.119 (3)0.0125 (14)0.0051 (18)0.033 (2)
C160.0656 (15)0.0760 (17)0.0626 (14)0.0174 (13)0.0230 (12)0.0226 (13)
C130.0667 (16)0.0620 (15)0.0862 (19)0.0004 (13)0.0217 (14)0.0329 (14)
C40.0681 (17)0.152 (3)0.0419 (13)0.022 (2)0.0114 (13)0.0159 (17)
C20.0611 (16)0.112 (3)0.083 (2)0.0126 (16)0.0182 (15)0.042 (2)
C30.0627 (16)0.167 (4)0.0518 (16)0.003 (2)0.0199 (13)0.030 (2)
C270.098 (3)0.127 (3)0.096 (3)0.027 (2)0.015 (2)0.012 (2)
Geometric parameters (Å, º) top
O4—C201.245 (3)C15—H150.9300
N1—C71.499 (2)C15—C161.376 (4)
N1—H1A0.89 (3)C23—H230.9300
N1—H1B0.93 (2)C23—C221.369 (3)
N1—H1C0.90 (3)C1—H10.9300
O2—C261.247 (3)C1—C21.395 (4)
O3—C201.252 (3)C10—H100.9300
N2—C81.484 (2)C10—C111.387 (3)
N2—H2A0.92 (3)C17—H170.9300
N2—H2B0.89 (3)C17—C161.378 (3)
N2—H2C0.89 (3)C22—H220.9300
N4—C191.334 (3)C22—C211.379 (3)
N4—C151.328 (3)C14—H140.9300
O1—C261.251 (3)C14—C131.391 (3)
N3—C251.336 (3)N5—C281.134 (5)
N3—C211.335 (3)C21—H210.9300
C19—H190.9300C12—H120.9300
C19—C181.385 (3)C12—C111.364 (4)
C20—C181.505 (3)C12—C131.360 (4)
C26—C241.508 (3)C11—H110.9300
C9—C81.516 (2)C5—H50.9300
C9—C101.386 (3)C5—C41.405 (4)
C9—C141.384 (3)C28—C271.437 (6)
C18—C171.377 (3)C16—H160.9300
C24—C251.385 (3)C13—H130.9300
C24—C231.389 (3)C4—H40.9300
C8—H80.9800C4—C31.371 (6)
C8—C71.542 (2)C2—H20.9300
C7—H70.9800C2—C31.342 (6)
C7—C61.520 (2)C3—H30.9300
C25—H250.9300C27—H27A0.9600
C6—C11.382 (3)C27—H27B0.9600
C6—C51.375 (3)C27—H27C0.9600
C7—N1—H1A113.7 (15)C24—C23—H23120.3
C7—N1—H1B107.1 (13)C22—C23—C24119.49 (19)
C7—N1—H1C106.4 (15)C22—C23—H23120.3
H1A—N1—H1B111 (2)C6—C1—H1120.0
H1A—N1—H1C111 (2)C6—C1—C2119.9 (3)
H1B—N1—H1C107 (2)C2—C1—H1120.0
C8—N2—H2A114.7 (17)C9—C10—H10119.4
C8—N2—H2B111.7 (16)C9—C10—C11121.3 (2)
C8—N2—H2C109.5 (15)C11—C10—H10119.4
H2A—N2—H2B106 (2)C18—C17—H17120.4
H2A—N2—H2C111 (2)C18—C17—C16119.1 (2)
H2B—N2—H2C103 (2)C16—C17—H17120.4
C15—N4—C19116.97 (18)C23—C22—H22120.8
C21—N3—C25117.43 (18)C23—C22—C21118.3 (2)
N4—C19—H19118.1C21—C22—H22120.8
N4—C19—C18123.78 (19)C9—C14—H14120.0
C18—C19—H19118.1C9—C14—C13120.1 (2)
O4—C20—O3126.26 (19)C13—C14—H14120.0
O4—C20—C18116.95 (17)N3—C21—C22123.6 (2)
O3—C20—C18116.78 (18)N3—C21—H21118.2
O2—C26—O1126.39 (19)C22—C21—H21118.2
O2—C26—C24118.71 (17)C11—C12—H12120.0
O1—C26—C24114.90 (18)C13—C12—H12120.0
C10—C9—C8119.10 (17)C13—C12—C11119.9 (2)
C14—C9—C8122.84 (17)C10—C11—H11120.1
C14—C9—C10117.97 (18)C12—C11—C10119.8 (2)
C19—C18—C20120.34 (18)C12—C11—H11120.1
C17—C18—C19117.87 (19)C6—C5—H5120.3
C17—C18—C20121.78 (18)C6—C5—C4119.5 (3)
C25—C24—C26121.48 (17)C4—C5—H5120.3
C25—C24—C23118.05 (17)N5—C28—C27178.2 (4)
C23—C24—C26120.46 (17)C15—C16—C17118.6 (2)
N2—C8—C9108.20 (14)C15—C16—H16120.7
N2—C8—H8107.8C17—C16—H16120.7
N2—C8—C7111.23 (14)C14—C13—H13119.5
C9—C8—H8107.8C12—C13—C14120.9 (2)
C9—C8—C7113.89 (14)C12—C13—H13119.5
C7—C8—H8107.8C5—C4—H4119.7
N1—C7—C8112.00 (14)C3—C4—C5120.6 (3)
N1—C7—H7107.8C3—C4—H4119.7
N1—C7—C6109.17 (14)C1—C2—H2119.4
C8—C7—H7107.8C3—C2—C1121.1 (3)
C6—C7—C8112.16 (14)C3—C2—H2119.4
C6—C7—H7107.8C4—C3—H3120.2
N3—C25—C24123.08 (18)C2—C3—C4119.6 (3)
N3—C25—H25118.5C2—C3—H3120.2
C24—C25—H25118.5C28—C27—H27A109.5
C1—C6—C7120.12 (19)C28—C27—H27B109.5
C5—C6—C7120.6 (2)C28—C27—H27C109.5
C5—C6—C1119.2 (2)H27A—C27—H27B109.5
N4—C15—H15118.2H27A—C27—H27C109.5
N4—C15—C16123.6 (2)H27B—C27—H27C109.5
C16—C15—H15118.2
(DPEN1-INA2) top
Crystal data top
C14H18N2·2(C6H4NO2)Dx = 1.012 Mg m3
Mr = 458.51Cu Kα radiation, λ = 1.54178 Å
Hexagonal, P6522Cell parameters from 2017 reflections
a = 13.854 (3) Åθ = 2–20°
c = 27.167 (8) ŵ = 0.57 mm1
V = 4516 (2) Å3T = 293 K
Z = 6Block, colourless
F(000) = 1452
Data collection top
Bruker P4
diffractometer
θmax = 70.0°, θmin = 6.1°
34749 measured reflectionsh = 1416
2862 independent reflectionsk = 1616
1940 reflections with I > 2σ(I)l = 3332
Rint = 0.061
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.2696P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.10 e Å3
2862 reflectionsΔρmin = 0.11 e Å3
166 parametersAbsolute structure: Flack x determined using 605 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraintsAbsolute structure parameter: 0.45 (13)
Primary atom site location: structure-invariant direct methods
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.45838 (18)0.1044 (2)0.52518 (7)0.0460 (5)
C130.3352 (2)0.0398 (2)0.52234 (7)0.0441 (6)
H130.30820.00630.55210.053*
C110.2865 (2)0.1146 (2)0.52192 (8)0.0503 (7)
C120.3315 (3)0.2090 (2)0.49233 (8)0.0593 (8)
H120.39090.22450.47160.071*
C70.2894 (3)0.2788 (3)0.49357 (10)0.0777 (11)
H70.32200.34330.47460.093*
C80.2002 (4)0.2549 (4)0.52221 (13)0.0948 (12)
H80.17100.30250.52250.114*
C90.1531 (4)0.1611 (4)0.55075 (16)0.1033 (13)
H90.09080.14400.56980.124*
C100.1977 (3)0.0922 (3)0.55126 (11)0.0747 (9)
H100.16740.03000.57170.090*
O10.5498 (2)0.3887 (2)0.39974 (7)0.0906 (8)
O20.5103 (2)0.5136 (3)0.42527 (8)0.1048 (10)
N10.7383 (2)0.5002 (2)0.56347 (8)0.0651 (7)
C60.5553 (3)0.4562 (3)0.42988 (9)0.0614 (8)
C30.6193 (2)0.4708 (2)0.47701 (8)0.0539 (7)
C20.6211 (3)0.5390 (3)0.51406 (10)0.0738 (10)
H20.58210.57720.51080.089*
C10.6816 (3)0.5503 (3)0.55635 (10)0.0765 (10)
H10.68170.59660.58110.092*
C50.7351 (3)0.4335 (3)0.52789 (10)0.0710 (9)
H50.77430.39590.53240.085*
C40.6770 (3)0.4163 (3)0.48445 (9)0.0650 (8)
H40.67730.36830.46060.078*
H2A0.478 (2)0.169 (3)0.5465 (10)0.066 (8)*
H2B0.488 (2)0.060 (2)0.5450 (11)0.074 (9)*
H2C0.494 (3)0.123 (3)0.4931 (12)0.084 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0584 (15)0.0467 (13)0.0285 (9)0.0229 (12)0.0019 (9)0.0020 (10)
C130.0575 (17)0.0445 (15)0.0229 (9)0.0200 (13)0.0018 (10)0.0013 (9)
C110.0669 (18)0.0555 (17)0.0313 (11)0.0326 (15)0.0033 (12)0.0055 (12)
C120.085 (2)0.0624 (19)0.0342 (12)0.0399 (18)0.0064 (13)0.0019 (12)
C70.126 (3)0.080 (2)0.0471 (15)0.066 (2)0.0103 (18)0.0005 (15)
C80.133 (4)0.109 (3)0.083 (2)0.091 (3)0.008 (2)0.002 (2)
C90.108 (3)0.134 (4)0.098 (3)0.083 (3)0.024 (2)0.007 (3)
C100.085 (2)0.082 (2)0.0671 (17)0.049 (2)0.0175 (16)0.0087 (16)
O10.135 (2)0.118 (2)0.0490 (11)0.0857 (18)0.0425 (12)0.0331 (12)
O20.134 (2)0.143 (2)0.0788 (16)0.101 (2)0.0552 (16)0.0435 (15)
N10.0586 (16)0.0864 (18)0.0429 (11)0.0307 (15)0.0124 (11)0.0057 (12)
C60.066 (2)0.075 (2)0.0408 (13)0.0342 (18)0.0139 (13)0.0035 (14)
C30.0509 (17)0.0662 (18)0.0383 (12)0.0246 (15)0.0073 (12)0.0033 (12)
C20.078 (2)0.107 (3)0.0518 (15)0.057 (2)0.0209 (15)0.0256 (16)
C10.080 (2)0.106 (3)0.0477 (15)0.050 (2)0.0209 (15)0.0285 (16)
C50.078 (2)0.084 (2)0.0515 (15)0.0413 (19)0.0174 (14)0.0109 (15)
C40.073 (2)0.080 (2)0.0443 (14)0.0403 (19)0.0149 (14)0.0136 (14)
Geometric parameters (Å, º) top
N2—C131.481 (3)C9—C101.373 (5)
N2—H2A0.99 (3)C10—H100.9300
N2—H2B1.05 (3)O1—C61.217 (3)
N2—H2C0.97 (3)O2—C61.236 (3)
C13—C13i1.544 (4)N1—C11.295 (4)
C13—H130.9800N1—C51.323 (4)
C13—C111.494 (4)C6—C31.512 (3)
C11—C121.389 (4)C3—C21.373 (4)
C11—C101.364 (4)C3—C41.362 (4)
C12—H120.9300C2—H20.9300
C12—C71.356 (4)C2—C11.385 (4)
C7—H70.9300C1—H10.9300
C7—C81.354 (5)C5—H50.9300
C8—H80.9300C5—C41.380 (4)
C8—C91.367 (6)C4—H40.9300
C9—H90.9300
C13—N2—H2A106.6 (17)C8—C9—C10120.0 (4)
C13—N2—H2B110.1 (16)C10—C9—H9120.0
C13—N2—H2C113.0 (19)C11—C10—C9120.2 (3)
H2A—N2—H2B103 (2)C11—C10—H10119.9
H2A—N2—H2C114 (2)C9—C10—H10119.9
H2B—N2—H2C109 (2)C1—N1—C5116.6 (2)
N2—C13—C13i111.41 (14)O1—C6—O2124.6 (3)
N2—C13—H13107.5O1—C6—C3118.6 (3)
N2—C13—C11111.4 (2)O2—C6—C3116.7 (3)
C13i—C13—H13107.5C2—C3—C6121.3 (3)
C11—C13—C13i111.45 (15)C4—C3—C6121.3 (3)
C11—C13—H13107.5C4—C3—C2117.4 (2)
C12—C11—C13120.8 (2)C3—C2—H2120.4
C10—C11—C13120.4 (3)C3—C2—C1119.1 (3)
C10—C11—C12118.8 (3)C1—C2—H2120.4
C11—C12—H12119.8N1—C1—C2124.0 (3)
C7—C12—C11120.4 (3)N1—C1—H1118.0
C7—C12—H12119.8C2—C1—H1118.0
C12—C7—H7119.8N1—C5—H5118.0
C8—C7—C12120.4 (3)N1—C5—C4123.9 (3)
C8—C7—H7119.8C4—C5—H5118.0
C7—C8—H8119.9C3—C4—C5119.0 (3)
C7—C8—C9120.1 (4)C3—C4—H4120.5
C9—C8—H8119.9C5—C4—H4120.5
C8—C9—H9120.0
N2—C13—C11—C1245.0 (3)O1—C6—C3—C2174.8 (3)
N2—C13—C11—C10134.0 (2)O1—C6—C3—C44.9 (4)
C13i—C13—C11—C1280.1 (3)O2—C6—C3—C24.1 (5)
C13i—C13—C11—C10101.0 (3)O2—C6—C3—C4176.2 (3)
C13—C11—C12—C7177.5 (2)N1—C5—C4—C30.2 (5)
C13—C11—C10—C9179.9 (3)C6—C3—C2—C1179.5 (3)
C11—C12—C7—C82.6 (5)C6—C3—C4—C5179.3 (3)
C12—C11—C10—C91.1 (5)C3—C2—C1—N10.3 (6)
C12—C7—C8—C91.1 (5)C2—C3—C4—C51.0 (4)
C7—C8—C9—C101.5 (6)C1—N1—C5—C40.9 (5)
C8—C9—C10—C112.5 (6)C5—N1—C1—C21.1 (5)
C10—C11—C12—C71.5 (4)C4—C3—C2—C10.8 (5)
Symmetry code: (i) xy, y, z+1.
 

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