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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 (1
R,2
R)-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 N
ammonium—H
N
pyridine 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 N
ammonium—H
N
pyridine 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
CCDC references: 1858712; 1858713; 1858714; 1858715
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).
Crystal data top
2(C6H4NO2)·2(C7H9N) | F(000) = 968 |
Mr = 458.51 | Dx = 1.164 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
a = 23.479 (6) Å | Cell parameters from 4568 reflections |
b = 8.602 (2) Å | θ = 3.4–28.0° |
c = 16.899 (4) Å | µ = 0.08 mm−1 |
β = 129.963 (5)° | T = 273 K |
V = 2616.1 (11) Å3 | Plate, colourless |
Z = 4 | 0.22 × 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 = 0.746 | h = −31→23 |
11704 measured reflections | k = −11→11 |
6271 independent reflections | l = −21→22 |
4303 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.03 | Δρmax = 0.33 e Å−3 |
6271 reflections | Δρmin = −0.22 e Å−3 |
368 parameters | Absolute structure: Flack x determined using 1504 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
37 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O2 | 0.36006 (14) | 0.4151 (3) | −0.0583 (2) | 0.0592 (7) | |
N1 | 0.06036 (16) | 0.7985 (3) | 0.1075 (2) | 0.0395 (6) | |
O1 | 0.46387 (13) | 0.4848 (4) | 0.0964 (2) | 0.0702 (8) | |
N3 | 0.34655 (16) | 0.6881 (4) | 0.1734 (2) | 0.0519 (7) | |
O4 | 0.55418 (17) | 0.5908 (4) | 0.4008 (2) | 0.0740 (8) | |
N2 | 0.5567 (2) | 0.6958 (4) | 0.6083 (2) | 0.0491 (7) | |
C24 | 0.34984 (17) | 0.5704 (4) | 0.0475 (3) | 0.0426 (7) | |
C25 | 0.38318 (17) | 0.6193 (4) | 0.1460 (2) | 0.0443 (7) | |
H25 | 0.434075 | 0.603958 | 0.196901 | 0.053* | |
O3 | 0.6230 (2) | 0.5019 (5) | 0.5614 (2) | 0.0989 (12) | |
C26 | 0.39509 (18) | 0.4843 (4) | 0.0268 (3) | 0.0444 (7) | |
C1 | 0.02056 (17) | 0.6499 (4) | 0.0586 (2) | 0.0428 (7) | |
H1 | −0.016651 | 0.638175 | 0.067326 | 0.051* | |
C2 | 0.0730 (2) | 0.5128 (4) | 0.1101 (3) | 0.0529 (9) | |
C23 | 0.2745 (2) | 0.5946 (5) | −0.0285 (3) | 0.0594 (10) | |
H23 | 0.250002 | 0.562070 | −0.095868 | 0.071* | |
N4 | 0.6549 (6) | 0.3071 (12) | 0.3295 (8) | 0.056 (2) | 0.697 (9) |
C19B | 0.613 (2) | 0.359 (4) | 0.355 (3) | 0.0446 (19) | 0.303 (9) |
H19B | 0.581400 | 0.436949 | 0.310247 | 0.054* | 0.303 (9) |
C9 | 0.5470 (2) | 0.9809 (5) | 0.6180 (3) | 0.0626 (10) | |
C21 | 0.2736 (2) | 0.7098 (5) | 0.0978 (3) | 0.0608 (10) | |
H21 | 0.246632 | 0.755895 | 0.114457 | 0.073* | |
C8 | 0.5396 (2) | 0.8471 (4) | 0.5534 (3) | 0.0541 (8) | |
H8 | 0.575532 | 0.862826 | 0.542585 | 0.065* | |
C22 | 0.2365 (2) | 0.6679 (6) | −0.0025 (3) | 0.0718 (12) | |
H22 | 0.186058 | 0.688648 | −0.052725 | 0.086* | |
C20 | 0.6035 (2) | 0.5057 (5) | 0.4732 (3) | 0.0582 (9) | |
C10 | 0.5144 (3) | 0.9734 (5) | 0.6628 (3) | 0.0783 (13) | |
H10 | 0.489349 | 0.883537 | 0.655269 | 0.094* | |
C7 | 0.1394 (2) | 0.5136 (6) | 0.1291 (4) | 0.0760 (12) | |
H7 | 0.153493 | 0.602058 | 0.113754 | 0.091* | |
C5 | 0.1658 (4) | 0.2554 (8) | 0.1931 (4) | 0.114 (2) | |
H5 | 0.197047 | 0.169215 | 0.221018 | 0.136* | |
C18 | 0.6457 (5) | 0.4124 (8) | 0.4513 (6) | 0.0442 (14) | 0.697 (9) |
C14 | 0.5840 (3) | 1.1139 (6) | 0.6308 (4) | 0.0904 (16) | |
H14 | 0.607081 | 1.122377 | 0.602366 | 0.108* | |
C13 | 0.5867 (4) | 1.2392 (7) | 0.6881 (5) | 0.113 (2) | |
H13 | 0.611721 | 1.329757 | 0.696439 | 0.136* | |
C12 | 0.5549 (4) | 1.2304 (8) | 0.7294 (4) | 0.114 (3) | |
H12 | 0.557023 | 1.314264 | 0.766001 | 0.137* | |
C3 | 0.0529 (3) | 0.3806 (6) | 0.1334 (4) | 0.0831 (14) | |
H3 | 0.008544 | 0.376911 | 0.121888 | 0.100* | |
C11 | 0.5182 (4) | 1.0963 (7) | 0.7184 (4) | 0.105 (2) | |
H11 | 0.496156 | 1.088745 | 0.748277 | 0.126* | |
C4 | 0.1012 (5) | 0.2513 (6) | 0.1750 (4) | 0.109 (2) | |
H4 | 0.087904 | 0.161355 | 0.190344 | 0.131* | |
C6 | 0.1855 (3) | 0.3859 (8) | 0.1702 (5) | 0.1039 (19) | |
H6 | 0.230194 | 0.388828 | 0.182542 | 0.125* | |
C17 | 0.7090 (6) | 0.3336 (10) | 0.5287 (5) | 0.082 (3) | 0.697 (9) |
H17 | 0.727066 | 0.340833 | 0.596231 | 0.099* | 0.697 (9) |
C15 | 0.7153 (5) | 0.2325 (11) | 0.4041 (5) | 0.087 (3) | 0.697 (9) |
H15 | 0.738824 | 0.169534 | 0.387973 | 0.105* | 0.697 (9) |
C16 | 0.7456 (6) | 0.2443 (13) | 0.5068 (6) | 0.106 (3) | 0.697 (9) |
H16 | 0.789426 | 0.193072 | 0.558921 | 0.127* | 0.697 (9) |
H1A | 0.029 (2) | 0.865 (4) | 0.095 (3) | 0.039 (9)* | |
H2A | 0.593 (2) | 0.709 (5) | 0.684 (3) | 0.054 (10)* | |
H1B | 0.095 (2) | 0.796 (5) | 0.181 (3) | 0.053 (10)* | |
H2B | 0.569 (2) | 0.633 (5) | 0.587 (3) | 0.056 (11)* | |
H2C | 0.513 (3) | 0.651 (6) | 0.595 (3) | 0.076 (14)* | |
H1C | 0.090 (2) | 0.842 (5) | 0.086 (3) | 0.061 (11)* | |
N4A | 0.6332 (14) | 0.256 (3) | 0.317 (2) | 0.075 (7) | 0.303 (9) |
C16A | 0.6984 (12) | 0.138 (3) | 0.4858 (13) | 0.106 (3) | 0.303 (9) |
H16A | 0.729839 | 0.059747 | 0.531243 | 0.127* | 0.303 (9) |
C17A | 0.6776 (10) | 0.254 (3) | 0.5184 (14) | 0.075 (5) | 0.303 (9) |
H17A | 0.694052 | 0.256027 | 0.585209 | 0.089* | 0.303 (9) |
C18A | 0.6330 (13) | 0.365 (2) | 0.4502 (17) | 0.0442 (14) | 0.303 (9) |
C15A | 0.6727 (13) | 0.138 (3) | 0.3859 (15) | 0.100 (6) | 0.303 (9) |
H15A | 0.683080 | 0.051385 | 0.364104 | 0.120* | 0.303 (9) |
C19 | 0.6209 (8) | 0.3949 (13) | 0.3519 (11) | 0.0446 (19) | 0.697 (9) |
H19 | 0.578199 | 0.447667 | 0.298441 | 0.054* | 0.697 (9) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0528 (14) | 0.0744 (17) | 0.0612 (15) | −0.0098 (12) | 0.0415 (13) | −0.0195 (13) |
N1 | 0.0370 (13) | 0.0497 (17) | 0.0330 (14) | 0.0019 (12) | 0.0230 (12) | −0.0002 (11) |
O1 | 0.0453 (13) | 0.096 (2) | 0.0649 (16) | 0.0140 (14) | 0.0333 (13) | −0.0145 (16) |
N3 | 0.0546 (16) | 0.0577 (18) | 0.0505 (15) | 0.0115 (14) | 0.0370 (14) | 0.0044 (14) |
O4 | 0.0850 (19) | 0.0796 (19) | 0.0675 (18) | 0.0266 (17) | 0.0536 (16) | 0.0121 (15) |
N2 | 0.0636 (19) | 0.0490 (18) | 0.0390 (16) | 0.0033 (14) | 0.0349 (16) | 0.0009 (13) |
C24 | 0.0418 (16) | 0.0439 (17) | 0.0466 (18) | 0.0043 (14) | 0.0304 (15) | 0.0042 (14) |
C25 | 0.0373 (15) | 0.052 (2) | 0.0412 (17) | 0.0080 (14) | 0.0242 (14) | 0.0015 (14) |
O3 | 0.128 (3) | 0.116 (3) | 0.0622 (18) | 0.048 (2) | 0.0659 (19) | 0.0099 (19) |
C26 | 0.0459 (17) | 0.0477 (18) | 0.0506 (19) | 0.0007 (14) | 0.0361 (16) | −0.0005 (16) |
C1 | 0.0405 (15) | 0.0543 (19) | 0.0359 (15) | −0.0028 (14) | 0.0257 (13) | 0.0018 (14) |
C2 | 0.057 (2) | 0.049 (2) | 0.0370 (17) | −0.0013 (16) | 0.0231 (16) | 0.0008 (15) |
C23 | 0.0462 (18) | 0.077 (3) | 0.0434 (18) | 0.0069 (18) | 0.0236 (15) | −0.0065 (18) |
N4 | 0.058 (5) | 0.063 (5) | 0.037 (4) | 0.007 (3) | 0.025 (4) | −0.006 (3) |
C19B | 0.043 (4) | 0.047 (6) | 0.038 (2) | 0.002 (4) | 0.023 (2) | 0.008 (4) |
C9 | 0.077 (3) | 0.045 (2) | 0.0391 (18) | 0.0009 (18) | 0.0249 (18) | 0.0029 (15) |
C21 | 0.054 (2) | 0.073 (3) | 0.067 (2) | 0.0183 (18) | 0.0441 (19) | 0.003 (2) |
C8 | 0.071 (2) | 0.049 (2) | 0.0439 (17) | −0.0058 (17) | 0.0374 (17) | 0.0011 (15) |
C22 | 0.0394 (18) | 0.099 (3) | 0.057 (2) | 0.018 (2) | 0.0216 (17) | −0.002 (2) |
C20 | 0.065 (2) | 0.061 (2) | 0.050 (2) | 0.004 (2) | 0.0376 (19) | −0.0047 (19) |
C10 | 0.123 (4) | 0.055 (2) | 0.059 (2) | 0.007 (2) | 0.059 (3) | −0.002 (2) |
C7 | 0.066 (2) | 0.071 (3) | 0.080 (3) | 0.019 (2) | 0.042 (2) | 0.011 (2) |
C5 | 0.111 (5) | 0.064 (3) | 0.071 (3) | 0.024 (3) | 0.015 (3) | −0.004 (3) |
C18 | 0.053 (4) | 0.037 (4) | 0.0405 (19) | 0.000 (3) | 0.029 (2) | 0.003 (3) |
C14 | 0.097 (3) | 0.065 (3) | 0.068 (3) | −0.017 (3) | 0.034 (3) | −0.003 (2) |
C13 | 0.115 (5) | 0.052 (3) | 0.079 (4) | −0.005 (3) | 0.019 (4) | −0.008 (3) |
C12 | 0.137 (6) | 0.072 (4) | 0.060 (3) | 0.024 (4) | 0.030 (3) | −0.013 (3) |
C3 | 0.092 (3) | 0.063 (3) | 0.059 (3) | −0.019 (2) | 0.032 (2) | 0.005 (2) |
C11 | 0.151 (5) | 0.076 (4) | 0.071 (3) | 0.027 (4) | 0.064 (3) | −0.006 (3) |
C4 | 0.138 (5) | 0.046 (3) | 0.070 (3) | −0.009 (3) | 0.034 (4) | 0.010 (2) |
C6 | 0.085 (3) | 0.088 (4) | 0.100 (4) | 0.031 (3) | 0.042 (3) | 0.004 (3) |
C17 | 0.111 (6) | 0.076 (5) | 0.037 (3) | 0.039 (4) | 0.037 (4) | 0.010 (3) |
C15 | 0.097 (5) | 0.101 (6) | 0.052 (3) | 0.052 (5) | 0.042 (4) | 0.007 (4) |
C16 | 0.108 (5) | 0.119 (6) | 0.057 (3) | 0.068 (4) | 0.038 (4) | 0.011 (4) |
N4A | 0.065 (14) | 0.089 (18) | 0.036 (7) | 0.028 (10) | 0.016 (9) | −0.009 (10) |
C16A | 0.108 (5) | 0.119 (6) | 0.057 (3) | 0.068 (4) | 0.038 (4) | 0.011 (4) |
C17A | 0.071 (8) | 0.097 (11) | 0.067 (8) | 0.035 (7) | 0.049 (7) | 0.013 (8) |
C18A | 0.053 (4) | 0.037 (4) | 0.0405 (19) | 0.000 (3) | 0.029 (2) | 0.003 (3) |
C15A | 0.109 (11) | 0.105 (11) | 0.080 (9) | 0.038 (9) | 0.058 (8) | −0.007 (8) |
C19 | 0.043 (4) | 0.047 (6) | 0.038 (2) | 0.002 (4) | 0.023 (2) | 0.008 (4) |
Geometric parameters (Å, º) top
O2—C26 | 1.257 (4) | C22—H22 | 0.9300 |
N1—C1 | 1.482 (4) | C20—C18 | 1.492 (9) |
N1—H1A | 0.85 (4) | C20—C18A | 1.56 (2) |
N1—H1B | 0.95 (4) | C10—H10 | 0.9300 |
N1—H1C | 1.04 (4) | C10—C11 | 1.378 (7) |
O1—C26 | 1.246 (4) | C7—H7 | 0.9300 |
N3—C25 | 1.347 (4) | C7—C6 | 1.376 (7) |
N3—C21 | 1.338 (5) | C5—H5 | 0.9300 |
O4—C20 | 1.246 (5) | C5—C4 | 1.344 (10) |
N2—C8 | 1.496 (5) | C5—C6 | 1.361 (11) |
N2—H2A | 0.99 (4) | C18—C17 | 1.371 (11) |
N2—H2B | 0.80 (5) | C18—C19 | 1.389 (17) |
N2—H2C | 0.97 (5) | C14—H14 | 0.9300 |
C24—C25 | 1.374 (5) | C14—C13 | 1.422 (9) |
C24—C26 | 1.509 (4) | C13—H13 | 0.9300 |
C24—C23 | 1.379 (5) | C13—C12 | 1.314 (11) |
C25—H25 | 0.9300 | C12—H12 | 0.9300 |
O3—C20 | 1.248 (5) | C12—C11 | 1.378 (10) |
C1—C1i | 1.549 (6) | C3—H3 | 0.9300 |
C1—H1 | 0.9800 | C3—C4 | 1.411 (9) |
C1—C2 | 1.513 (5) | C11—H11 | 0.9300 |
C2—C7 | 1.375 (6) | C4—H4 | 0.9300 |
C2—C3 | 1.383 (6) | C6—H6 | 0.9300 |
C23—H23 | 0.9300 | C17—H17 | 0.9300 |
C23—C22 | 1.375 (6) | C17—C16 | 1.370 (11) |
N4—C15 | 1.310 (13) | C15—H15 | 0.9300 |
N4—C19 | 1.32 (2) | C15—C16 | 1.394 (10) |
C19B—H19B | 0.9300 | C16—H16 | 0.9300 |
C19B—N4A | 1.34 (5) | N4A—C15A | 1.36 (4) |
C19B—C18A | 1.35 (5) | C16A—H16A | 0.9300 |
C9—C8 | 1.517 (6) | C16A—C17A | 1.37 (2) |
C9—C10 | 1.380 (7) | C16A—C15A | 1.38 (3) |
C9—C14 | 1.367 (7) | C17A—H17A | 0.9300 |
C21—H21 | 0.9300 | C17A—C18A | 1.33 (3) |
C21—C22 | 1.366 (6) | C15A—H15A | 0.9300 |
C8—C8ii | 1.551 (8) | C19—H19 | 0.9300 |
C8—H8 | 0.9800 | | |
| | | |
C1—N1—H1A | 107 (2) | C9—C10—H10 | 119.3 |
C1—N1—H1B | 114 (2) | C11—C10—C9 | 121.5 (5) |
C1—N1—H1C | 116 (2) | C11—C10—H10 | 119.3 |
H1A—N1—H1B | 103 (3) | C2—C7—H7 | 119.4 |
H1A—N1—H1C | 110 (3) | C2—C7—C6 | 121.3 (5) |
H1B—N1—H1C | 105 (3) | C6—C7—H7 | 119.4 |
C21—N3—C25 | 116.2 (3) | C4—C5—H5 | 120.1 |
C8—N2—H2A | 112 (2) | C4—C5—C6 | 119.8 (5) |
C8—N2—H2B | 110 (3) | C6—C5—H5 | 120.1 |
C8—N2—H2C | 112 (3) | C17—C18—C20 | 121.0 (7) |
H2A—N2—H2B | 114 (4) | C17—C18—C19 | 117.0 (9) |
H2A—N2—H2C | 104 (3) | C19—C18—C20 | 121.9 (9) |
H2B—N2—H2C | 105 (4) | C9—C14—H14 | 120.4 |
C25—C24—C26 | 119.6 (3) | C9—C14—C13 | 119.3 (6) |
C25—C24—C23 | 118.3 (3) | C13—C14—H14 | 120.4 |
C23—C24—C26 | 122.0 (3) | C14—C13—H13 | 119.1 |
N3—C25—C24 | 123.9 (3) | C12—C13—C14 | 121.7 (6) |
N3—C25—H25 | 118.0 | C12—C13—H13 | 119.1 |
C24—C25—H25 | 118.0 | C13—C12—H12 | 120.2 |
O2—C26—C24 | 117.2 (3) | C13—C12—C11 | 119.7 (6) |
O1—C26—O2 | 125.5 (3) | C11—C12—H12 | 120.2 |
O1—C26—C24 | 117.3 (3) | C2—C3—H3 | 120.7 |
N1—C1—C1i | 111.42 (18) | C2—C3—C4 | 118.7 (6) |
N1—C1—H1 | 108.0 | C4—C3—H3 | 120.7 |
N1—C1—C2 | 111.2 (2) | C10—C11—H11 | 120.1 |
C1i—C1—H1 | 108.0 | C12—C11—C10 | 119.7 (6) |
C2—C1—C1i | 110.1 (2) | C12—C11—H11 | 120.1 |
C2—C1—H1 | 108.0 | C5—C4—C3 | 121.3 (6) |
C7—C2—C1 | 120.9 (4) | C5—C4—H4 | 119.3 |
C7—C2—C3 | 118.7 (4) | C3—C4—H4 | 119.3 |
C3—C2—C1 | 120.3 (4) | C7—C6—H6 | 119.9 |
C24—C23—H23 | 120.7 | C5—C6—C7 | 120.2 (6) |
C22—C23—C24 | 118.6 (3) | C5—C6—H6 | 119.9 |
C22—C23—H23 | 120.7 | C18—C17—H17 | 119.9 |
C15—N4—C19 | 119.0 (11) | C16—C17—C18 | 120.3 (7) |
N4A—C19B—H19B | 115.3 | C16—C17—H17 | 119.9 |
N4A—C19B—C18A | 129 (3) | N4—C15—H15 | 118.9 |
C18A—C19B—H19B | 115.3 | N4—C15—C16 | 122.2 (8) |
C10—C9—C8 | 120.8 (4) | C16—C15—H15 | 118.9 |
C14—C9—C8 | 121.1 (4) | C17—C16—C15 | 118.1 (6) |
C14—C9—C10 | 118.1 (4) | C17—C16—H16 | 121.0 |
N3—C21—H21 | 118.3 | C15—C16—H16 | 121.0 |
N3—C21—C22 | 123.5 (3) | C19B—N4A—C15A | 110 (3) |
C22—C21—H21 | 118.3 | C17A—C16A—H16A | 119.8 |
N2—C8—C9 | 110.7 (3) | C17A—C16A—C15A | 120.3 (17) |
N2—C8—C8ii | 111.4 (2) | C15A—C16A—H16A | 119.8 |
N2—C8—H8 | 108.4 | C16A—C17A—H17A | 121.4 |
C9—C8—C8ii | 109.5 (3) | C18A—C17A—C16A | 117.1 (17) |
C9—C8—H8 | 108.4 | C18A—C17A—H17A | 121.4 |
C8ii—C8—H8 | 108.4 | C19B—C18A—C20 | 117 (2) |
C23—C22—H22 | 120.3 | C17A—C18A—C19B | 119 (2) |
C21—C22—C23 | 119.4 (3) | C17A—C18A—C20 | 124.4 (18) |
C21—C22—H22 | 120.3 | N4A—C15A—C16A | 124 (2) |
O4—C20—O3 | 125.7 (4) | N4A—C15A—H15A | 117.9 |
O4—C20—C18 | 114.8 (4) | C16A—C15A—H15A | 117.9 |
O4—C20—C18A | 119.5 (9) | N4—C19—C18 | 123.3 (12) |
O3—C20—C18 | 119.3 (5) | N4—C19—H19 | 118.3 |
O3—C20—C18A | 113.3 (9) | C18—C19—H19 | 118.3 |
| | | |
N1—C1—C2—C7 | −48.1 (4) | C9—C14—C13—C12 | 0.3 (9) |
N1—C1—C2—C3 | 135.7 (4) | C21—N3—C25—C24 | −0.8 (5) |
N3—C21—C22—C23 | 2.3 (8) | C8—C9—C10—C11 | −177.5 (4) |
O4—C20—C18—C17 | 169.3 (7) | C8—C9—C14—C13 | 177.2 (4) |
O4—C20—C18—C19 | −13.9 (8) | C20—C18—C17—C16 | 177.8 (9) |
O4—C20—C18A—C19B | 12 (2) | C20—C18—C19—N4 | −176.6 (7) |
O4—C20—C18A—C17A | −170.3 (16) | C10—C9—C8—N2 | −47.9 (5) |
C24—C23—C22—C21 | −2.1 (7) | C10—C9—C8—C8ii | 75.3 (5) |
C25—N3—C21—C22 | −0.8 (6) | C10—C9—C14—C13 | −0.8 (7) |
C25—C24—C26—O2 | 166.1 (3) | C7—C2—C3—C4 | −0.5 (7) |
C25—C24—C26—O1 | −12.3 (5) | C18—C17—C16—C15 | −2.0 (17) |
C25—C24—C23—C22 | 0.7 (6) | C14—C9—C8—N2 | 134.1 (4) |
O3—C20—C18—C17 | −5.7 (9) | C14—C9—C8—C8ii | −102.7 (5) |
O3—C20—C18—C19 | 171.1 (6) | C14—C9—C10—C11 | 0.5 (7) |
O3—C20—C18A—C19B | 179.0 (17) | C14—C13—C12—C11 | 0.6 (10) |
O3—C20—C18A—C17A | −3 (2) | C13—C12—C11—C10 | −0.9 (9) |
C26—C24—C25—N3 | −175.7 (3) | C3—C2—C7—C6 | 0.1 (7) |
C26—C24—C23—C22 | 177.1 (4) | C4—C5—C6—C7 | 0.1 (10) |
C1i—C1—C2—C7 | 75.9 (4) | C6—C5—C4—C3 | −0.5 (10) |
C1i—C1—C2—C3 | −100.3 (4) | C17—C18—C19—N4 | 0.3 (11) |
C1—C2—C7—C6 | −176.1 (4) | C15—N4—C19—C18 | −0.3 (13) |
C1—C2—C3—C4 | 175.8 (4) | N4A—C19B—C18A—C20 | 177 (2) |
C2—C7—C6—C5 | 0.0 (9) | N4A—C19B—C18A—C17A | −1 (4) |
C2—C3—C4—C5 | 0.7 (8) | C16A—C17A—C18A—C19B | −2 (3) |
C23—C24—C25—N3 | 0.8 (6) | C16A—C17A—C18A—C20 | −180.0 (19) |
C23—C24—C26—O2 | −10.2 (5) | C17A—C16A—C15A—N4A | 7 (4) |
C23—C24—C26—O1 | 171.4 (4) | C18A—C19B—N4A—C15A | 7 (4) |
N4—C15—C16—C17 | 2.1 (18) | C15A—C16A—C17A—C18A | −1 (4) |
C19B—N4A—C15A—C16A | −10 (4) | C19—N4—C15—C16 | −0.9 (16) |
C9—C10—C11—C12 | 0.4 (8) | C19—C18—C17—C16 | 0.9 (14) |
Symmetry codes: (i) −x, y, −z; (ii) −x+1, y, −z+1. |
Crystal data top
2(C6H4NO2)·2(C7H9N)·C4H8O2 | F(000) = 1160 |
Mr = 546.61 | Dx = 1.211 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71076 Å |
a = 22.9673 (11) Å | Cell parameters from 9833 reflections |
b = 8.8676 (4) Å | θ = 3.1–28.3° |
c = 16.7749 (8) Å | µ = 0.09 mm−1 |
β = 118.613 (2)° | T = 273 K |
V = 2999.2 (2) Å3 | Needle, colourless |
Z = 4 | 0.23 × 0.17 × 0.09 mm |
Data collection top
CCD area detector diffractometer | θmax = 28.3°, θmin = 3.1° |
25955 measured reflections | h = −30→30 |
7385 independent reflections | k = −11→11 |
6427 reflections with I > 2σ(I) | l = −22→22 |
Rint = 0.023 | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.06 | Δρmax = 0.55 e Å−3 |
7385 reflections | Δρmin = −0.35 e Å−3 |
387 parameters | Absolute structure: Flack x determined using 2721 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute 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 | x | y | z | Uiso*/Ueq | |
O4 | 0.54861 (12) | 0.4041 (3) | 0.18285 (15) | 0.0606 (5) | |
O1 | 0.46407 (11) | 0.5224 (3) | 0.34732 (15) | 0.0642 (6) | |
O3 | 0.59492 (11) | 0.5086 (3) | 0.10566 (14) | 0.0611 (5) | |
O2 | 0.37176 (12) | 0.5937 (3) | 0.34938 (16) | 0.0703 (7) | |
N2 | 0.45082 (11) | 0.2941 (3) | 0.02723 (14) | 0.0406 (4) | |
N1 | 0.55293 (12) | 0.6970 (3) | 0.47865 (15) | 0.0430 (5) | |
N3 | 0.35886 (12) | 0.3121 (3) | 0.09945 (16) | 0.0548 (6) | |
N4 | 0.62868 (13) | 0.7213 (3) | 0.38490 (16) | 0.0543 (6) | |
C14 | 0.51476 (12) | 0.8387 (3) | 0.46704 (15) | 0.0408 (5) | |
H14 | 0.4779 | 0.8411 | 0.4048 | 0.049* | |
C7 | 0.46490 (10) | 0.1472 (3) | −0.00403 (14) | 0.0365 (5) | |
H7 | 0.4321 | 0.1323 | −0.0679 | 0.044* | |
C25 | 0.60351 (14) | 0.6194 (3) | 0.31861 (18) | 0.0466 (5) | |
H25 | 0.5753 | 0.5464 | 0.3209 | 0.056* | |
C20 | 0.40245 (14) | 0.5266 (3) | 0.31496 (17) | 0.0469 (5) | |
C6 | 0.45964 (11) | 0.0172 (3) | 0.05089 (16) | 0.0390 (5) | |
C24 | 0.61697 (12) | 0.6156 (3) | 0.24625 (16) | 0.0403 (5) | |
C5 | 0.48820 (15) | 0.0263 (4) | 0.14490 (18) | 0.0510 (6) | |
H5 | 0.5092 | 0.1148 | 0.1745 | 0.061* | |
C19 | 0.39182 (12) | 0.3822 (3) | 0.17957 (18) | 0.0463 (6) | |
H19 | 0.4378 | 0.3876 | 0.2058 | 0.056* | |
O5 | 0.24709 (16) | 0.8768 (4) | 0.2538 (2) | 0.0899 (9) | |
C18 | 0.36205 (13) | 0.4471 (3) | 0.22577 (17) | 0.0438 (5) | |
C26 | 0.58409 (13) | 0.4997 (3) | 0.17210 (17) | 0.0457 (5) | |
C13 | 0.55717 (14) | 0.9772 (3) | 0.48090 (19) | 0.0473 (6) | |
C15 | 0.29348 (16) | 0.3055 (5) | 0.0632 (2) | 0.0670 (9) | |
H15 | 0.2697 | 0.2557 | 0.0081 | 0.080* | |
C12 | 0.53189 (18) | 1.0991 (4) | 0.4225 (3) | 0.0660 (8) | |
H12 | 0.4895 | 1.0945 | 0.3730 | 0.079* | |
C17 | 0.29360 (16) | 0.4399 (5) | 0.1857 (2) | 0.0647 (9) | |
H17 | 0.2712 | 0.4825 | 0.2139 | 0.078* | |
C1 | 0.42890 (15) | −0.1152 (4) | 0.0083 (2) | 0.0558 (7) | |
H1 | 0.4096 | −0.1227 | −0.0546 | 0.067* | |
O6 | 0.18450 (18) | 0.6719 (5) | 0.1952 (3) | 0.1238 (16) | |
C23 | 0.65908 (15) | 0.7241 (3) | 0.2441 (2) | 0.0511 (6) | |
H23 | 0.6692 | 0.7261 | 0.1967 | 0.061* | |
C4 | 0.4855 (2) | −0.0956 (4) | 0.1946 (2) | 0.0669 (9) | |
H4 | 0.5052 | −0.0890 | 0.2575 | 0.080* | |
C21 | 0.66925 (17) | 0.8255 (4) | 0.3812 (2) | 0.0599 (7) | |
H21 | 0.6868 | 0.8980 | 0.4268 | 0.072* | |
C8 | 0.62067 (16) | 0.9859 (4) | 0.5537 (2) | 0.0623 (8) | |
H8 | 0.6380 | 0.9049 | 0.5935 | 0.075* | |
C11 | 0.5700 (3) | 1.2277 (5) | 0.4381 (4) | 0.0922 (14) | |
H11 | 0.5529 | 1.3100 | 0.3993 | 0.111* | |
C16 | 0.25914 (16) | 0.3682 (6) | 0.1029 (3) | 0.0784 (12) | |
H16 | 0.2131 | 0.3626 | 0.0744 | 0.094* | |
C22 | 0.68621 (19) | 0.8301 (4) | 0.3129 (2) | 0.0621 (8) | |
H22 | 0.7153 | 0.9031 | 0.3130 | 0.074* | |
C3 | 0.4540 (2) | −0.2268 (4) | 0.1515 (3) | 0.0696 (9) | |
H3 | 0.4512 | −0.3073 | 0.1850 | 0.084* | |
C10 | 0.6323 (3) | 1.2345 (5) | 0.5097 (4) | 0.0994 (16) | |
H10 | 0.6575 | 1.3214 | 0.5196 | 0.119* | |
C2 | 0.42661 (18) | −0.2378 (4) | 0.0587 (3) | 0.0703 (9) | |
H2 | 0.4065 | −0.3272 | 0.0295 | 0.084* | |
C9 | 0.6583 (2) | 1.1138 (5) | 0.5675 (3) | 0.0871 (12) | |
H9 | 0.7012 | 1.1186 | 0.6158 | 0.105* | |
C29 | 0.2110 (2) | 0.7601 (6) | 0.2574 (4) | 0.0903 (14) | |
C30 | 0.2089 (3) | 0.7562 (7) | 0.3430 (5) | 0.1121 (18) | |
H30A | 0.2506 | 0.7205 | 0.3905 | 0.168* | |
H30B | 0.1741 | 0.6897 | 0.3372 | 0.168* | |
H30C | 0.2005 | 0.8558 | 0.3576 | 0.168* | |
C28 | 0.2540 (3) | 0.8910 (13) | 0.1735 (4) | 0.145 (3) | |
H28A | 0.2472 | 0.7930 | 0.1447 | 0.174* | |
H28B | 0.2199 | 0.9583 | 0.1312 | 0.174* | |
C27 | 0.3163 (4) | 0.9466 (14) | 0.1914 (6) | 0.162 (4) | |
H27A | 0.3202 | 0.9427 | 0.1370 | 0.243* | |
H27B | 0.3505 | 0.8860 | 0.2375 | 0.243* | |
H27C | 0.3209 | 1.0490 | 0.2121 | 0.243* | |
H2A | 0.4351 (15) | 0.368 (4) | −0.024 (2) | 0.046 (8)* | |
H1A | 0.5765 (18) | 0.714 (4) | 0.455 (2) | 0.052 (8)* | |
H1B | 0.5791 (15) | 0.661 (4) | 0.538 (2) | 0.042 (7)* | |
H2B | 0.4195 (19) | 0.282 (4) | 0.043 (2) | 0.059 (9)* | |
H1C | 0.523 (2) | 0.622 (5) | 0.444 (3) | 0.061 (10)* | |
H2C | 0.490 (2) | 0.331 (5) | 0.085 (3) | 0.075 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.0688 (13) | 0.0592 (12) | 0.0578 (11) | −0.0176 (10) | 0.0333 (10) | −0.0136 (10) |
O1 | 0.0528 (11) | 0.0734 (14) | 0.0601 (12) | −0.0070 (11) | 0.0220 (9) | −0.0216 (11) |
O3 | 0.0729 (13) | 0.0692 (14) | 0.0512 (10) | −0.0082 (11) | 0.0378 (10) | −0.0121 (10) |
O2 | 0.0702 (14) | 0.0864 (17) | 0.0565 (12) | 0.0071 (12) | 0.0321 (11) | −0.0224 (12) |
N2 | 0.0413 (10) | 0.0492 (12) | 0.0428 (10) | 0.0042 (8) | 0.0294 (9) | 0.0036 (9) |
N1 | 0.0464 (11) | 0.0498 (12) | 0.0409 (10) | −0.0021 (9) | 0.0275 (9) | −0.0011 (9) |
N3 | 0.0513 (12) | 0.0741 (17) | 0.0505 (12) | −0.0074 (11) | 0.0337 (10) | −0.0131 (11) |
N4 | 0.0638 (14) | 0.0602 (14) | 0.0512 (12) | −0.0083 (12) | 0.0373 (11) | −0.0080 (11) |
C14 | 0.0425 (11) | 0.0474 (13) | 0.0330 (10) | 0.0007 (10) | 0.0183 (9) | 0.0026 (9) |
C7 | 0.0317 (10) | 0.0485 (13) | 0.0318 (9) | −0.0003 (9) | 0.0174 (8) | −0.0023 (9) |
C25 | 0.0510 (13) | 0.0471 (13) | 0.0511 (13) | −0.0050 (11) | 0.0319 (11) | 0.0001 (11) |
C20 | 0.0549 (14) | 0.0444 (13) | 0.0444 (12) | 0.0002 (11) | 0.0263 (11) | −0.0041 (10) |
C6 | 0.0344 (10) | 0.0461 (12) | 0.0418 (11) | 0.0002 (9) | 0.0226 (9) | −0.0001 (10) |
C24 | 0.0413 (11) | 0.0410 (12) | 0.0412 (11) | 0.0033 (9) | 0.0219 (9) | 0.0020 (9) |
C5 | 0.0631 (15) | 0.0524 (15) | 0.0420 (12) | −0.0008 (13) | 0.0288 (11) | 0.0032 (11) |
C19 | 0.0405 (11) | 0.0573 (15) | 0.0489 (13) | −0.0042 (11) | 0.0276 (10) | −0.0074 (11) |
O5 | 0.0809 (17) | 0.108 (2) | 0.0699 (16) | −0.0042 (18) | 0.0271 (13) | −0.0195 (16) |
C18 | 0.0441 (12) | 0.0482 (13) | 0.0449 (12) | −0.0013 (10) | 0.0260 (10) | −0.0022 (10) |
C26 | 0.0458 (12) | 0.0481 (14) | 0.0444 (12) | 0.0035 (11) | 0.0225 (10) | −0.0029 (10) |
C13 | 0.0516 (13) | 0.0490 (14) | 0.0469 (13) | 0.0002 (11) | 0.0282 (11) | 0.0046 (11) |
C15 | 0.0562 (16) | 0.098 (3) | 0.0490 (14) | −0.0160 (17) | 0.0270 (13) | −0.0205 (16) |
C12 | 0.0634 (18) | 0.0617 (18) | 0.073 (2) | 0.0058 (15) | 0.0325 (16) | 0.0179 (16) |
C17 | 0.0488 (15) | 0.092 (2) | 0.0655 (18) | −0.0001 (15) | 0.0370 (14) | −0.0173 (17) |
C1 | 0.0471 (13) | 0.0615 (17) | 0.0616 (16) | −0.0116 (12) | 0.0284 (12) | −0.0122 (14) |
O6 | 0.078 (2) | 0.110 (3) | 0.142 (3) | 0.0076 (19) | 0.020 (2) | −0.049 (3) |
C23 | 0.0620 (16) | 0.0517 (15) | 0.0546 (14) | −0.0001 (12) | 0.0401 (13) | 0.0032 (12) |
C4 | 0.083 (2) | 0.070 (2) | 0.0585 (17) | 0.0135 (18) | 0.0425 (17) | 0.0195 (16) |
C21 | 0.0733 (19) | 0.0537 (16) | 0.0619 (16) | −0.0144 (14) | 0.0398 (15) | −0.0157 (14) |
C8 | 0.0565 (16) | 0.0574 (18) | 0.0618 (17) | −0.0095 (14) | 0.0194 (14) | 0.0050 (14) |
C11 | 0.103 (3) | 0.054 (2) | 0.127 (4) | 0.005 (2) | 0.061 (3) | 0.033 (2) |
C16 | 0.0409 (14) | 0.126 (4) | 0.0682 (19) | −0.0060 (19) | 0.0259 (14) | −0.022 (2) |
C22 | 0.078 (2) | 0.0504 (16) | 0.0760 (19) | −0.0186 (15) | 0.0519 (17) | −0.0089 (15) |
C3 | 0.075 (2) | 0.0544 (17) | 0.095 (3) | 0.0074 (16) | 0.054 (2) | 0.0207 (18) |
C10 | 0.090 (3) | 0.063 (2) | 0.140 (4) | −0.024 (2) | 0.050 (3) | 0.001 (3) |
C2 | 0.0625 (18) | 0.0484 (16) | 0.108 (3) | −0.0109 (14) | 0.048 (2) | −0.0080 (18) |
C9 | 0.068 (2) | 0.076 (3) | 0.096 (3) | −0.022 (2) | 0.022 (2) | −0.001 (2) |
C29 | 0.058 (2) | 0.081 (3) | 0.103 (3) | 0.018 (2) | 0.015 (2) | −0.026 (2) |
C30 | 0.128 (5) | 0.081 (3) | 0.137 (5) | 0.012 (3) | 0.071 (4) | 0.014 (3) |
C28 | 0.111 (4) | 0.248 (10) | 0.079 (3) | 0.009 (6) | 0.048 (3) | −0.023 (5) |
C27 | 0.127 (5) | 0.223 (10) | 0.141 (6) | −0.006 (6) | 0.067 (5) | 0.058 (7) |
Geometric parameters (Å, º) top
O4—C26 | 1.247 (4) | C15—H15 | 0.9300 |
O1—C20 | 1.250 (3) | C15—C16 | 1.370 (5) |
O3—C26 | 1.255 (3) | C12—H12 | 0.9300 |
O2—C20 | 1.254 (3) | C12—C11 | 1.384 (6) |
N2—C7 | 1.496 (3) | C17—H17 | 0.9300 |
N2—H2A | 1.00 (3) | C17—C16 | 1.380 (5) |
N2—H2B | 0.88 (4) | C1—H1 | 0.9300 |
N2—H2C | 1.01 (4) | C1—C2 | 1.393 (5) |
N1—C14 | 1.491 (3) | O6—C29 | 1.209 (6) |
N1—H1A | 0.82 (4) | C23—H23 | 0.9300 |
N1—H1B | 0.95 (3) | C23—C22 | 1.384 (4) |
N1—H1C | 0.94 (4) | C4—H4 | 0.9300 |
N3—C19 | 1.338 (4) | C4—C3 | 1.377 (6) |
N3—C15 | 1.324 (4) | C21—H21 | 0.9300 |
N4—C25 | 1.331 (4) | C21—C22 | 1.376 (4) |
N4—C21 | 1.335 (4) | C8—H8 | 0.9300 |
C14—C14i | 1.549 (4) | C8—C9 | 1.377 (5) |
C14—H14 | 0.9800 | C11—H11 | 0.9300 |
C14—C13 | 1.514 (4) | C11—C10 | 1.359 (8) |
C7—C7ii | 1.552 (4) | C16—H16 | 0.9300 |
C7—H7 | 0.9800 | C22—H22 | 0.9300 |
C7—C6 | 1.516 (3) | C3—H3 | 0.9300 |
C25—H25 | 0.9300 | C3—C2 | 1.376 (6) |
C25—C24 | 1.389 (3) | C10—H10 | 0.9300 |
C20—C18 | 1.506 (4) | C10—C9 | 1.373 (7) |
C6—C5 | 1.390 (3) | C2—H2 | 0.9300 |
C6—C1 | 1.380 (4) | C9—H9 | 0.9300 |
C24—C26 | 1.508 (4) | C29—C30 | 1.461 (8) |
C24—C23 | 1.377 (4) | C30—H30A | 0.9600 |
C5—H5 | 0.9300 | C30—H30B | 0.9600 |
C5—C4 | 1.385 (4) | C30—H30C | 0.9600 |
C19—H19 | 0.9300 | C28—H28A | 0.9700 |
C19—C18 | 1.381 (3) | C28—H28B | 0.9700 |
O5—C29 | 1.345 (6) | C28—C27 | 1.404 (11) |
O5—C28 | 1.436 (6) | C27—H27A | 0.9600 |
C18—C17 | 1.384 (4) | C27—H27B | 0.9600 |
C13—C12 | 1.385 (4) | C27—H27C | 0.9600 |
C13—C8 | 1.385 (4) | | |
| | | |
C7—N2—H2A | 108.6 (19) | C18—C17—H17 | 120.6 |
C7—N2—H2B | 110 (3) | C16—C17—C18 | 118.8 (3) |
C7—N2—H2C | 112 (3) | C16—C17—H17 | 120.6 |
H2A—N2—H2B | 109 (3) | C6—C1—H1 | 119.7 |
H2A—N2—H2C | 113 (3) | C6—C1—C2 | 120.5 (3) |
H2B—N2—H2C | 104 (3) | C2—C1—H1 | 119.7 |
C14—N1—H1A | 105 (3) | C24—C23—H23 | 120.2 |
C14—N1—H1B | 117.5 (19) | C24—C23—C22 | 119.6 (2) |
C14—N1—H1C | 108 (2) | C22—C23—H23 | 120.2 |
H1A—N1—H1B | 110 (3) | C5—C4—H4 | 119.7 |
H1A—N1—H1C | 107 (3) | C3—C4—C5 | 120.5 (3) |
H1B—N1—H1C | 109 (3) | C3—C4—H4 | 119.7 |
C15—N3—C19 | 117.0 (2) | N4—C21—H21 | 118.6 |
C25—N4—C21 | 117.7 (2) | N4—C21—C22 | 122.8 (3) |
N1—C14—C14i | 109.73 (14) | C22—C21—H21 | 118.6 |
N1—C14—H14 | 108.1 | C13—C8—H8 | 119.9 |
N1—C14—C13 | 111.6 (2) | C9—C8—C13 | 120.3 (3) |
C14i—C14—H14 | 108.1 | C9—C8—H8 | 119.9 |
C13—C14—C14i | 111.07 (16) | C12—C11—H11 | 119.8 |
C13—C14—H14 | 108.1 | C10—C11—C12 | 120.4 (4) |
N2—C7—C7ii | 111.06 (14) | C10—C11—H11 | 119.8 |
N2—C7—H7 | 108.6 | C15—C16—C17 | 119.3 (3) |
N2—C7—C6 | 110.81 (18) | C15—C16—H16 | 120.4 |
C7ii—C7—H7 | 108.6 | C17—C16—H16 | 120.4 |
C6—C7—C7ii | 109.19 (16) | C23—C22—H22 | 120.7 |
C6—C7—H7 | 108.6 | C21—C22—C23 | 118.7 (3) |
N4—C25—H25 | 118.1 | C21—C22—H22 | 120.7 |
N4—C25—C24 | 123.8 (2) | C4—C3—H3 | 120.2 |
C24—C25—H25 | 118.1 | C2—C3—C4 | 119.6 (3) |
O1—C20—O2 | 125.7 (3) | C2—C3—H3 | 120.2 |
O1—C20—C18 | 116.6 (2) | C11—C10—H10 | 119.8 |
O2—C20—C18 | 117.7 (2) | C11—C10—C9 | 120.5 (4) |
C5—C6—C7 | 120.9 (2) | C9—C10—H10 | 119.8 |
C1—C6—C7 | 120.1 (2) | C1—C2—H2 | 119.9 |
C1—C6—C5 | 118.9 (3) | C3—C2—C1 | 120.1 (3) |
C25—C24—C26 | 120.3 (2) | C3—C2—H2 | 119.9 |
C23—C24—C25 | 117.3 (2) | C8—C9—H9 | 120.1 |
C23—C24—C26 | 122.4 (2) | C10—C9—C8 | 119.9 (4) |
C6—C5—H5 | 119.9 | C10—C9—H9 | 120.1 |
C4—C5—C6 | 120.3 (3) | O5—C29—C30 | 111.9 (4) |
C4—C5—H5 | 119.9 | O6—C29—O5 | 121.7 (6) |
N3—C19—H19 | 117.9 | O6—C29—C30 | 126.4 (6) |
N3—C19—C18 | 124.3 (2) | C29—C30—H30A | 109.5 |
C18—C19—H19 | 117.9 | C29—C30—H30B | 109.5 |
C29—O5—C28 | 117.2 (5) | C29—C30—H30C | 109.5 |
C19—C18—C20 | 121.2 (2) | H30A—C30—H30B | 109.5 |
C19—C18—C17 | 117.4 (2) | H30A—C30—H30C | 109.5 |
C17—C18—C20 | 121.4 (2) | H30B—C30—H30C | 109.5 |
O4—C26—O3 | 126.3 (3) | O5—C28—H28A | 109.0 |
O4—C26—C24 | 116.6 (2) | O5—C28—H28B | 109.0 |
O3—C26—C24 | 117.1 (2) | H28A—C28—H28B | 107.8 |
C12—C13—C14 | 120.2 (3) | C27—C28—O5 | 112.9 (6) |
C8—C13—C14 | 120.6 (3) | C27—C28—H28A | 109.0 |
C8—C13—C12 | 119.2 (3) | C27—C28—H28B | 109.0 |
N3—C15—H15 | 118.3 | C28—C27—H27A | 109.5 |
N3—C15—C16 | 123.3 (3) | C28—C27—H27B | 109.5 |
C16—C15—H15 | 118.3 | C28—C27—H27C | 109.5 |
C13—C12—H12 | 120.1 | H27A—C27—H27B | 109.5 |
C11—C12—C13 | 119.8 (4) | H27A—C27—H27C | 109.5 |
C11—C12—H12 | 120.1 | H27B—C27—H27C | 109.5 |
Symmetry codes: (i) −x+1, y, −z+1; (ii) −x+1, y, −z. |
Crystal data top
2(C6H4NO2)·C14H18N2·C2H3N | Dx = 1.213 Mg m−3 |
Mr = 499.56 | Mo Kα radiation, λ = 0.71076 Å |
Orthorhombic, P212121 | Cell parameters from 6368 reflections |
a = 11.770 (8) Å | θ = 3.0–28.3° |
b = 14.079 (10) Å | µ = 0.08 mm−1 |
c = 16.502 (12) Å | T = 273 K |
V = 2734 (3) Å3 | Plate, colourless |
Z = 4 | 0.16 × 0.14 × 0.11 mm |
F(000) = 1056 | |
Data collection top
CCD area detector diffractometer | θmax = 28.5°, θmin = 2.9° |
50039 measured reflections | h = −15→15 |
6822 independent reflections | k = −18→18 |
5953 reflections with I > 2σ(I) | l = −22→22 |
Rint = 0.033 | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.02 | Δρmax = 0.18 e Å−3 |
6822 reflections | Δρmin = −0.15 e Å−3 |
359 parameters | Absolute structure: Flack x determined using 2398 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
O4 | 0.64925 (16) | 0.33234 (12) | 0.53942 (10) | 0.0618 (4) | |
N1 | 0.40239 (13) | 0.47996 (11) | 0.60982 (9) | 0.0324 (3) | |
O2 | 0.36217 (14) | 0.66424 (11) | 0.55123 (10) | 0.0550 (4) | |
O3 | 0.48724 (15) | 0.38030 (12) | 0.48295 (10) | 0.0583 (4) | |
N2 | 0.63956 (13) | 0.50560 (12) | 0.60726 (9) | 0.0346 (3) | |
N4 | 0.69423 (15) | 0.12510 (12) | 0.36712 (11) | 0.0461 (4) | |
O1 | 0.55086 (16) | 0.65893 (14) | 0.53993 (13) | 0.0743 (6) | |
N3 | 0.35530 (15) | 0.90372 (14) | 0.40284 (14) | 0.0575 (5) | |
C19 | 0.67551 (17) | 0.19076 (13) | 0.42384 (12) | 0.0414 (4) | |
H19 | 0.7224 | 0.1912 | 0.4692 | 0.050* | |
C20 | 0.57422 (18) | 0.32924 (14) | 0.48634 (12) | 0.0432 (4) | |
C26 | 0.45537 (18) | 0.69471 (14) | 0.52644 (11) | 0.0419 (4) | |
C9 | 0.66486 (14) | 0.47029 (13) | 0.75030 (11) | 0.0346 (4) | |
C18 | 0.59025 (16) | 0.25829 (13) | 0.41911 (12) | 0.0389 (4) | |
C24 | 0.45687 (16) | 0.78237 (13) | 0.47390 (11) | 0.0374 (4) | |
C8 | 0.58324 (13) | 0.50966 (12) | 0.68766 (10) | 0.0309 (3) | |
H8 | 0.5697 | 0.5766 | 0.7007 | 0.037* | |
C7 | 0.46710 (14) | 0.45902 (12) | 0.68598 (10) | 0.0315 (3) | |
H7 | 0.4812 | 0.3905 | 0.6878 | 0.038* | |
C25 | 0.35733 (17) | 0.82754 (15) | 0.45106 (13) | 0.0456 (5) | |
H25 | 0.2887 | 0.8037 | 0.4702 | 0.055* | |
C6 | 0.39406 (15) | 0.48467 (16) | 0.75875 (11) | 0.0404 (4) | |
C15 | 0.6282 (2) | 0.12765 (17) | 0.30187 (15) | 0.0540 (5) | |
H15 | 0.6406 | 0.0829 | 0.2614 | 0.065* | |
C23 | 0.55903 (17) | 0.81906 (15) | 0.44570 (14) | 0.0488 (5) | |
H23 | 0.6275 | 0.7910 | 0.4605 | 0.059* | |
C1 | 0.3506 (2) | 0.57543 (19) | 0.76651 (16) | 0.0574 (6) | |
H1 | 0.3689 | 0.6218 | 0.7285 | 0.069* | |
C10 | 0.74631 (18) | 0.52982 (15) | 0.78345 (13) | 0.0473 (5) | |
H10 | 0.7473 | 0.5936 | 0.7688 | 0.057* | |
C17 | 0.5228 (2) | 0.25882 (18) | 0.35092 (15) | 0.0584 (6) | |
H17 | 0.4647 | 0.3031 | 0.3455 | 0.070* | |
C22 | 0.5582 (2) | 0.89685 (19) | 0.39597 (18) | 0.0637 (7) | |
H22 | 0.6256 | 0.9221 | 0.3760 | 0.076* | |
C14 | 0.6659 (2) | 0.37565 (17) | 0.77302 (16) | 0.0580 (6) | |
H14 | 0.6135 | 0.3336 | 0.7508 | 0.070* | |
N5 | 0.5680 (3) | 0.7209 (2) | 0.8327 (3) | 0.1104 (12) | |
C21 | 0.4548 (2) | 0.93689 (18) | 0.37629 (18) | 0.0652 (7) | |
H21 | 0.4545 | 0.9899 | 0.3427 | 0.078* | |
C12 | 0.8243 (2) | 0.4030 (2) | 0.86100 (15) | 0.0627 (6) | |
H12 | 0.8767 | 0.3805 | 0.8985 | 0.075* | |
C11 | 0.8264 (2) | 0.4961 (2) | 0.83805 (14) | 0.0599 (6) | |
H11 | 0.8813 | 0.5368 | 0.8589 | 0.072* | |
C5 | 0.3668 (2) | 0.4173 (2) | 0.81580 (14) | 0.0608 (6) | |
H5 | 0.3957 | 0.3560 | 0.8116 | 0.073* | |
C28 | 0.5718 (3) | 0.6687 (3) | 0.8850 (3) | 0.0829 (10) | |
C16 | 0.5425 (2) | 0.1928 (2) | 0.29087 (16) | 0.0681 (7) | |
H16 | 0.4988 | 0.1924 | 0.2439 | 0.082* | |
C13 | 0.7453 (2) | 0.3433 (2) | 0.82899 (19) | 0.0716 (8) | |
H13 | 0.7444 | 0.2799 | 0.8448 | 0.086* | |
C4 | 0.2951 (3) | 0.4417 (3) | 0.88055 (17) | 0.0875 (11) | |
H4 | 0.2769 | 0.3964 | 0.9195 | 0.105* | |
C2 | 0.2793 (3) | 0.5974 (3) | 0.8314 (2) | 0.0853 (10) | |
H2 | 0.2506 | 0.6587 | 0.8363 | 0.102* | |
C3 | 0.2516 (3) | 0.5317 (4) | 0.88688 (19) | 0.0939 (12) | |
H3 | 0.2030 | 0.5471 | 0.9294 | 0.113* | |
C27 | 0.5764 (4) | 0.6001 (3) | 0.9494 (3) | 0.1070 (13) | |
H27A | 0.6063 | 0.5414 | 0.9290 | 0.161* | |
H27B | 0.5013 | 0.5898 | 0.9703 | 0.161* | |
H27C | 0.6246 | 0.6234 | 0.9919 | 0.161* | |
H1A | 0.395 (2) | 0.5417 (18) | 0.5997 (14) | 0.043 (6)* | |
H1B | 0.4397 (19) | 0.4490 (16) | 0.5677 (14) | 0.040 (5)* | |
H1C | 0.334 (2) | 0.4522 (17) | 0.6156 (14) | 0.046 (6)* | |
H2A | 0.645 (2) | 0.446 (2) | 0.5853 (17) | 0.061 (7)* | |
H2B | 0.710 (2) | 0.5282 (18) | 0.6092 (14) | 0.050 (6)* | |
H2C | 0.605 (2) | 0.5452 (17) | 0.5731 (15) | 0.046 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.0726 (11) | 0.0595 (10) | 0.0534 (9) | 0.0190 (8) | −0.0116 (8) | −0.0151 (7) |
N1 | 0.0282 (6) | 0.0349 (8) | 0.0342 (7) | −0.0010 (6) | 0.0017 (6) | −0.0017 (6) |
O2 | 0.0555 (9) | 0.0461 (8) | 0.0634 (9) | 0.0062 (7) | 0.0115 (8) | 0.0161 (7) |
O3 | 0.0625 (9) | 0.0610 (9) | 0.0515 (8) | 0.0241 (8) | −0.0004 (7) | −0.0128 (7) |
N2 | 0.0265 (6) | 0.0382 (8) | 0.0389 (8) | 0.0005 (6) | 0.0020 (6) | 0.0094 (6) |
N4 | 0.0416 (9) | 0.0397 (8) | 0.0571 (10) | 0.0071 (7) | 0.0026 (8) | −0.0055 (7) |
O1 | 0.0578 (10) | 0.0721 (11) | 0.0929 (13) | 0.0241 (9) | 0.0051 (10) | 0.0417 (10) |
N3 | 0.0359 (8) | 0.0586 (11) | 0.0780 (13) | 0.0083 (8) | −0.0010 (9) | 0.0311 (10) |
C19 | 0.0401 (9) | 0.0405 (9) | 0.0437 (10) | 0.0033 (8) | −0.0010 (8) | 0.0014 (8) |
C20 | 0.0525 (11) | 0.0384 (9) | 0.0386 (9) | 0.0064 (8) | 0.0064 (8) | 0.0007 (7) |
C26 | 0.0487 (10) | 0.0386 (9) | 0.0385 (9) | 0.0113 (8) | 0.0029 (8) | 0.0051 (7) |
C9 | 0.0314 (8) | 0.0377 (9) | 0.0345 (8) | 0.0008 (7) | 0.0001 (7) | 0.0009 (7) |
C18 | 0.0391 (9) | 0.0360 (9) | 0.0417 (9) | 0.0029 (7) | 0.0033 (8) | 0.0002 (7) |
C24 | 0.0372 (8) | 0.0353 (8) | 0.0396 (9) | 0.0062 (7) | −0.0004 (8) | 0.0021 (7) |
C8 | 0.0291 (7) | 0.0264 (7) | 0.0373 (8) | −0.0005 (6) | 0.0007 (6) | 0.0002 (6) |
C7 | 0.0299 (7) | 0.0303 (7) | 0.0342 (8) | −0.0018 (6) | 0.0019 (7) | 0.0019 (6) |
C25 | 0.0326 (9) | 0.0479 (11) | 0.0562 (11) | 0.0029 (8) | 0.0025 (8) | 0.0166 (9) |
C6 | 0.0301 (8) | 0.0571 (11) | 0.0340 (8) | −0.0049 (8) | 0.0024 (7) | −0.0032 (8) |
C15 | 0.0496 (11) | 0.0537 (12) | 0.0587 (13) | 0.0050 (10) | −0.0012 (10) | −0.0194 (10) |
C23 | 0.0328 (9) | 0.0469 (11) | 0.0665 (13) | 0.0069 (8) | −0.0018 (9) | 0.0088 (9) |
C1 | 0.0491 (12) | 0.0626 (14) | 0.0604 (14) | 0.0057 (10) | 0.0116 (10) | −0.0149 (11) |
C10 | 0.0504 (11) | 0.0425 (10) | 0.0489 (11) | −0.0014 (9) | −0.0081 (9) | −0.0086 (9) |
C17 | 0.0528 (13) | 0.0584 (13) | 0.0641 (13) | 0.0219 (11) | −0.0149 (11) | −0.0122 (11) |
C22 | 0.0374 (10) | 0.0607 (14) | 0.0930 (19) | −0.0037 (10) | 0.0069 (11) | 0.0266 (13) |
C14 | 0.0522 (12) | 0.0449 (11) | 0.0769 (15) | −0.0076 (9) | −0.0218 (11) | 0.0174 (11) |
N5 | 0.109 (2) | 0.0587 (16) | 0.164 (3) | 0.0135 (16) | −0.015 (2) | −0.012 (2) |
C21 | 0.0448 (11) | 0.0590 (14) | 0.0916 (18) | 0.0026 (10) | 0.0031 (13) | 0.0397 (13) |
C12 | 0.0577 (14) | 0.0825 (17) | 0.0477 (12) | 0.0078 (12) | −0.0159 (11) | 0.0095 (12) |
C11 | 0.0549 (12) | 0.0704 (15) | 0.0545 (12) | 0.0024 (12) | −0.0179 (10) | −0.0189 (11) |
C5 | 0.0525 (12) | 0.0850 (17) | 0.0448 (11) | −0.0081 (12) | 0.0064 (10) | 0.0140 (12) |
C28 | 0.0654 (18) | 0.0644 (18) | 0.119 (3) | 0.0125 (14) | −0.0051 (18) | −0.033 (2) |
C16 | 0.0656 (15) | 0.0760 (17) | 0.0626 (14) | 0.0174 (13) | −0.0230 (12) | −0.0226 (13) |
C13 | 0.0667 (16) | 0.0620 (15) | 0.0862 (19) | −0.0004 (13) | −0.0217 (14) | 0.0329 (14) |
C4 | 0.0681 (17) | 0.152 (3) | 0.0419 (13) | −0.022 (2) | 0.0114 (13) | 0.0159 (17) |
C2 | 0.0611 (16) | 0.112 (3) | 0.083 (2) | 0.0126 (16) | 0.0182 (15) | −0.042 (2) |
C3 | 0.0627 (16) | 0.167 (4) | 0.0518 (16) | −0.003 (2) | 0.0199 (13) | −0.030 (2) |
C27 | 0.098 (3) | 0.127 (3) | 0.096 (3) | 0.027 (2) | 0.015 (2) | −0.012 (2) |
Geometric parameters (Å, º) top
O4—C20 | 1.245 (3) | C15—H15 | 0.9300 |
N1—C7 | 1.499 (2) | C15—C16 | 1.376 (4) |
N1—H1A | 0.89 (3) | C23—H23 | 0.9300 |
N1—H1B | 0.93 (2) | C23—C22 | 1.369 (3) |
N1—H1C | 0.90 (3) | C1—H1 | 0.9300 |
O2—C26 | 1.247 (3) | C1—C2 | 1.395 (4) |
O3—C20 | 1.252 (3) | C10—H10 | 0.9300 |
N2—C8 | 1.484 (2) | C10—C11 | 1.387 (3) |
N2—H2A | 0.92 (3) | C17—H17 | 0.9300 |
N2—H2B | 0.89 (3) | C17—C16 | 1.378 (3) |
N2—H2C | 0.89 (3) | C22—H22 | 0.9300 |
N4—C19 | 1.334 (3) | C22—C21 | 1.379 (3) |
N4—C15 | 1.328 (3) | C14—H14 | 0.9300 |
O1—C26 | 1.251 (3) | C14—C13 | 1.391 (3) |
N3—C25 | 1.336 (3) | N5—C28 | 1.134 (5) |
N3—C21 | 1.335 (3) | C21—H21 | 0.9300 |
C19—H19 | 0.9300 | C12—H12 | 0.9300 |
C19—C18 | 1.385 (3) | C12—C11 | 1.364 (4) |
C20—C18 | 1.505 (3) | C12—C13 | 1.360 (4) |
C26—C24 | 1.508 (3) | C11—H11 | 0.9300 |
C9—C8 | 1.516 (2) | C5—H5 | 0.9300 |
C9—C10 | 1.386 (3) | C5—C4 | 1.405 (4) |
C9—C14 | 1.384 (3) | C28—C27 | 1.437 (6) |
C18—C17 | 1.377 (3) | C16—H16 | 0.9300 |
C24—C25 | 1.385 (3) | C13—H13 | 0.9300 |
C24—C23 | 1.389 (3) | C4—H4 | 0.9300 |
C8—H8 | 0.9800 | C4—C3 | 1.371 (6) |
C8—C7 | 1.542 (2) | C2—H2 | 0.9300 |
C7—H7 | 0.9800 | C2—C3 | 1.342 (6) |
C7—C6 | 1.520 (2) | C3—H3 | 0.9300 |
C25—H25 | 0.9300 | C27—H27A | 0.9600 |
C6—C1 | 1.382 (3) | C27—H27B | 0.9600 |
C6—C5 | 1.375 (3) | C27—H27C | 0.9600 |
| | | |
C7—N1—H1A | 113.7 (15) | C24—C23—H23 | 120.3 |
C7—N1—H1B | 107.1 (13) | C22—C23—C24 | 119.49 (19) |
C7—N1—H1C | 106.4 (15) | C22—C23—H23 | 120.3 |
H1A—N1—H1B | 111 (2) | C6—C1—H1 | 120.0 |
H1A—N1—H1C | 111 (2) | C6—C1—C2 | 119.9 (3) |
H1B—N1—H1C | 107 (2) | C2—C1—H1 | 120.0 |
C8—N2—H2A | 114.7 (17) | C9—C10—H10 | 119.4 |
C8—N2—H2B | 111.7 (16) | C9—C10—C11 | 121.3 (2) |
C8—N2—H2C | 109.5 (15) | C11—C10—H10 | 119.4 |
H2A—N2—H2B | 106 (2) | C18—C17—H17 | 120.4 |
H2A—N2—H2C | 111 (2) | C18—C17—C16 | 119.1 (2) |
H2B—N2—H2C | 103 (2) | C16—C17—H17 | 120.4 |
C15—N4—C19 | 116.97 (18) | C23—C22—H22 | 120.8 |
C21—N3—C25 | 117.43 (18) | C23—C22—C21 | 118.3 (2) |
N4—C19—H19 | 118.1 | C21—C22—H22 | 120.8 |
N4—C19—C18 | 123.78 (19) | C9—C14—H14 | 120.0 |
C18—C19—H19 | 118.1 | C9—C14—C13 | 120.1 (2) |
O4—C20—O3 | 126.26 (19) | C13—C14—H14 | 120.0 |
O4—C20—C18 | 116.95 (17) | N3—C21—C22 | 123.6 (2) |
O3—C20—C18 | 116.78 (18) | N3—C21—H21 | 118.2 |
O2—C26—O1 | 126.39 (19) | C22—C21—H21 | 118.2 |
O2—C26—C24 | 118.71 (17) | C11—C12—H12 | 120.0 |
O1—C26—C24 | 114.90 (18) | C13—C12—H12 | 120.0 |
C10—C9—C8 | 119.10 (17) | C13—C12—C11 | 119.9 (2) |
C14—C9—C8 | 122.84 (17) | C10—C11—H11 | 120.1 |
C14—C9—C10 | 117.97 (18) | C12—C11—C10 | 119.8 (2) |
C19—C18—C20 | 120.34 (18) | C12—C11—H11 | 120.1 |
C17—C18—C19 | 117.87 (19) | C6—C5—H5 | 120.3 |
C17—C18—C20 | 121.78 (18) | C6—C5—C4 | 119.5 (3) |
C25—C24—C26 | 121.48 (17) | C4—C5—H5 | 120.3 |
C25—C24—C23 | 118.05 (17) | N5—C28—C27 | 178.2 (4) |
C23—C24—C26 | 120.46 (17) | C15—C16—C17 | 118.6 (2) |
N2—C8—C9 | 108.20 (14) | C15—C16—H16 | 120.7 |
N2—C8—H8 | 107.8 | C17—C16—H16 | 120.7 |
N2—C8—C7 | 111.23 (14) | C14—C13—H13 | 119.5 |
C9—C8—H8 | 107.8 | C12—C13—C14 | 120.9 (2) |
C9—C8—C7 | 113.89 (14) | C12—C13—H13 | 119.5 |
C7—C8—H8 | 107.8 | C5—C4—H4 | 119.7 |
N1—C7—C8 | 112.00 (14) | C3—C4—C5 | 120.6 (3) |
N1—C7—H7 | 107.8 | C3—C4—H4 | 119.7 |
N1—C7—C6 | 109.17 (14) | C1—C2—H2 | 119.4 |
C8—C7—H7 | 107.8 | C3—C2—C1 | 121.1 (3) |
C6—C7—C8 | 112.16 (14) | C3—C2—H2 | 119.4 |
C6—C7—H7 | 107.8 | C4—C3—H3 | 120.2 |
N3—C25—C24 | 123.08 (18) | C2—C3—C4 | 119.6 (3) |
N3—C25—H25 | 118.5 | C2—C3—H3 | 120.2 |
C24—C25—H25 | 118.5 | C28—C27—H27A | 109.5 |
C1—C6—C7 | 120.12 (19) | C28—C27—H27B | 109.5 |
C5—C6—C7 | 120.6 (2) | C28—C27—H27C | 109.5 |
C5—C6—C1 | 119.2 (2) | H27A—C27—H27B | 109.5 |
N4—C15—H15 | 118.2 | H27A—C27—H27C | 109.5 |
N4—C15—C16 | 123.6 (2) | H27B—C27—H27C | 109.5 |
C16—C15—H15 | 118.2 | | |
Crystal data top
C14H18N2·2(C6H4NO2) | Dx = 1.012 Mg m−3 |
Mr = 458.51 | Cu Kα radiation, λ = 1.54178 Å |
Hexagonal, P6522 | Cell parameters from 2017 reflections |
a = 13.854 (3) Å | θ = 2–20° |
c = 27.167 (8) Å | µ = 0.57 mm−1 |
V = 4516 (2) Å3 | T = 293 K |
Z = 6 | Block, colourless |
F(000) = 1452 | |
Data collection top
Bruker P4 diffractometer | θmax = 70.0°, θmin = 6.1° |
34749 measured reflections | h = −14→16 |
2862 independent reflections | k = −16→16 |
1940 reflections with I > 2σ(I) | l = −33→32 |
Rint = 0.061 | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.02 | Δρmax = 0.10 e Å−3 |
2862 reflections | Δρmin = −0.11 e Å−3 |
166 parameters | Absolute structure: Flack x determined using 605 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
N2 | 0.45838 (18) | 0.1044 (2) | 0.52518 (7) | 0.0460 (5) | |
C13 | 0.3352 (2) | 0.0398 (2) | 0.52234 (7) | 0.0441 (6) | |
H13 | 0.3082 | −0.0063 | 0.5521 | 0.053* | |
C11 | 0.2865 (2) | 0.1146 (2) | 0.52192 (8) | 0.0503 (7) | |
C12 | 0.3315 (3) | 0.2090 (2) | 0.49233 (8) | 0.0593 (8) | |
H12 | 0.3909 | 0.2245 | 0.4716 | 0.071* | |
C7 | 0.2894 (3) | 0.2788 (3) | 0.49357 (10) | 0.0777 (11) | |
H7 | 0.3220 | 0.3433 | 0.4746 | 0.093* | |
C8 | 0.2002 (4) | 0.2549 (4) | 0.52221 (13) | 0.0948 (12) | |
H8 | 0.1710 | 0.3025 | 0.5225 | 0.114* | |
C9 | 0.1531 (4) | 0.1611 (4) | 0.55075 (16) | 0.1033 (13) | |
H9 | 0.0908 | 0.1440 | 0.5698 | 0.124* | |
C10 | 0.1977 (3) | 0.0922 (3) | 0.55126 (11) | 0.0747 (9) | |
H10 | 0.1674 | 0.0300 | 0.5717 | 0.090* | |
O1 | 0.5498 (2) | 0.3887 (2) | 0.39974 (7) | 0.0906 (8) | |
O2 | 0.5103 (2) | 0.5136 (3) | 0.42527 (8) | 0.1048 (10) | |
N1 | 0.7383 (2) | 0.5002 (2) | 0.56347 (8) | 0.0651 (7) | |
C6 | 0.5553 (3) | 0.4562 (3) | 0.42988 (9) | 0.0614 (8) | |
C3 | 0.6193 (2) | 0.4708 (2) | 0.47701 (8) | 0.0539 (7) | |
C2 | 0.6211 (3) | 0.5390 (3) | 0.51406 (10) | 0.0738 (10) | |
H2 | 0.5821 | 0.5772 | 0.5108 | 0.089* | |
C1 | 0.6816 (3) | 0.5503 (3) | 0.55635 (10) | 0.0765 (10) | |
H1 | 0.6817 | 0.5966 | 0.5811 | 0.092* | |
C5 | 0.7351 (3) | 0.4335 (3) | 0.52789 (10) | 0.0710 (9) | |
H5 | 0.7743 | 0.3959 | 0.5324 | 0.085* | |
C4 | 0.6770 (3) | 0.4163 (3) | 0.48445 (9) | 0.0650 (8) | |
H4 | 0.6773 | 0.3683 | 0.4606 | 0.078* | |
H2A | 0.478 (2) | 0.169 (3) | 0.5465 (10) | 0.066 (8)* | |
H2B | 0.488 (2) | 0.060 (2) | 0.5450 (11) | 0.074 (9)* | |
H2C | 0.494 (3) | 0.123 (3) | 0.4931 (12) | 0.084 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N2 | 0.0584 (15) | 0.0467 (13) | 0.0285 (9) | 0.0229 (12) | −0.0019 (9) | −0.0020 (10) |
C13 | 0.0575 (17) | 0.0445 (15) | 0.0229 (9) | 0.0200 (13) | 0.0018 (10) | 0.0013 (9) |
C11 | 0.0669 (18) | 0.0555 (17) | 0.0313 (11) | 0.0326 (15) | −0.0033 (12) | −0.0055 (12) |
C12 | 0.085 (2) | 0.0624 (19) | 0.0342 (12) | 0.0399 (18) | −0.0064 (13) | −0.0019 (12) |
C7 | 0.126 (3) | 0.080 (2) | 0.0471 (15) | 0.066 (2) | −0.0103 (18) | −0.0005 (15) |
C8 | 0.133 (4) | 0.109 (3) | 0.083 (2) | 0.091 (3) | −0.008 (2) | 0.002 (2) |
C9 | 0.108 (3) | 0.134 (4) | 0.098 (3) | 0.083 (3) | 0.024 (2) | 0.007 (3) |
C10 | 0.085 (2) | 0.082 (2) | 0.0671 (17) | 0.049 (2) | 0.0175 (16) | 0.0087 (16) |
O1 | 0.135 (2) | 0.118 (2) | 0.0490 (11) | 0.0857 (18) | −0.0425 (12) | −0.0331 (12) |
O2 | 0.134 (2) | 0.143 (2) | 0.0788 (16) | 0.101 (2) | −0.0552 (16) | −0.0435 (15) |
N1 | 0.0586 (16) | 0.0864 (18) | 0.0429 (11) | 0.0307 (15) | −0.0124 (11) | −0.0057 (12) |
C6 | 0.066 (2) | 0.075 (2) | 0.0408 (13) | 0.0342 (18) | −0.0139 (13) | −0.0035 (14) |
C3 | 0.0509 (17) | 0.0662 (18) | 0.0383 (12) | 0.0246 (15) | −0.0073 (12) | −0.0033 (12) |
C2 | 0.078 (2) | 0.107 (3) | 0.0518 (15) | 0.057 (2) | −0.0209 (15) | −0.0256 (16) |
C1 | 0.080 (2) | 0.106 (3) | 0.0477 (15) | 0.050 (2) | −0.0209 (15) | −0.0285 (16) |
C5 | 0.078 (2) | 0.084 (2) | 0.0515 (15) | 0.0413 (19) | −0.0174 (14) | −0.0109 (15) |
C4 | 0.073 (2) | 0.080 (2) | 0.0443 (14) | 0.0403 (19) | −0.0149 (14) | −0.0136 (14) |
Geometric parameters (Å, º) top
N2—C13 | 1.481 (3) | C9—C10 | 1.373 (5) |
N2—H2A | 0.99 (3) | C10—H10 | 0.9300 |
N2—H2B | 1.05 (3) | O1—C6 | 1.217 (3) |
N2—H2C | 0.97 (3) | O2—C6 | 1.236 (3) |
C13—C13i | 1.544 (4) | N1—C1 | 1.295 (4) |
C13—H13 | 0.9800 | N1—C5 | 1.323 (4) |
C13—C11 | 1.494 (4) | C6—C3 | 1.512 (3) |
C11—C12 | 1.389 (4) | C3—C2 | 1.373 (4) |
C11—C10 | 1.364 (4) | C3—C4 | 1.362 (4) |
C12—H12 | 0.9300 | C2—H2 | 0.9300 |
C12—C7 | 1.356 (4) | C2—C1 | 1.385 (4) |
C7—H7 | 0.9300 | C1—H1 | 0.9300 |
C7—C8 | 1.354 (5) | C5—H5 | 0.9300 |
C8—H8 | 0.9300 | C5—C4 | 1.380 (4) |
C8—C9 | 1.367 (6) | C4—H4 | 0.9300 |
C9—H9 | 0.9300 | | |
| | | |
C13—N2—H2A | 106.6 (17) | C8—C9—C10 | 120.0 (4) |
C13—N2—H2B | 110.1 (16) | C10—C9—H9 | 120.0 |
C13—N2—H2C | 113.0 (19) | C11—C10—C9 | 120.2 (3) |
H2A—N2—H2B | 103 (2) | C11—C10—H10 | 119.9 |
H2A—N2—H2C | 114 (2) | C9—C10—H10 | 119.9 |
H2B—N2—H2C | 109 (2) | C1—N1—C5 | 116.6 (2) |
N2—C13—C13i | 111.41 (14) | O1—C6—O2 | 124.6 (3) |
N2—C13—H13 | 107.5 | O1—C6—C3 | 118.6 (3) |
N2—C13—C11 | 111.4 (2) | O2—C6—C3 | 116.7 (3) |
C13i—C13—H13 | 107.5 | C2—C3—C6 | 121.3 (3) |
C11—C13—C13i | 111.45 (15) | C4—C3—C6 | 121.3 (3) |
C11—C13—H13 | 107.5 | C4—C3—C2 | 117.4 (2) |
C12—C11—C13 | 120.8 (2) | C3—C2—H2 | 120.4 |
C10—C11—C13 | 120.4 (3) | C3—C2—C1 | 119.1 (3) |
C10—C11—C12 | 118.8 (3) | C1—C2—H2 | 120.4 |
C11—C12—H12 | 119.8 | N1—C1—C2 | 124.0 (3) |
C7—C12—C11 | 120.4 (3) | N1—C1—H1 | 118.0 |
C7—C12—H12 | 119.8 | C2—C1—H1 | 118.0 |
C12—C7—H7 | 119.8 | N1—C5—H5 | 118.0 |
C8—C7—C12 | 120.4 (3) | N1—C5—C4 | 123.9 (3) |
C8—C7—H7 | 119.8 | C4—C5—H5 | 118.0 |
C7—C8—H8 | 119.9 | C3—C4—C5 | 119.0 (3) |
C7—C8—C9 | 120.1 (4) | C3—C4—H4 | 120.5 |
C9—C8—H8 | 119.9 | C5—C4—H4 | 120.5 |
C8—C9—H9 | 120.0 | | |
| | | |
N2—C13—C11—C12 | 45.0 (3) | O1—C6—C3—C2 | −174.8 (3) |
N2—C13—C11—C10 | −134.0 (2) | O1—C6—C3—C4 | 4.9 (4) |
C13i—C13—C11—C12 | −80.1 (3) | O2—C6—C3—C2 | 4.1 (5) |
C13i—C13—C11—C10 | 101.0 (3) | O2—C6—C3—C4 | −176.2 (3) |
C13—C11—C12—C7 | −177.5 (2) | N1—C5—C4—C3 | 0.2 (5) |
C13—C11—C10—C9 | −179.9 (3) | C6—C3—C2—C1 | −179.5 (3) |
C11—C12—C7—C8 | −2.6 (5) | C6—C3—C4—C5 | 179.3 (3) |
C12—C11—C10—C9 | 1.1 (5) | C3—C2—C1—N1 | 0.3 (6) |
C12—C7—C8—C9 | 1.1 (5) | C2—C3—C4—C5 | −1.0 (4) |
C7—C8—C9—C10 | 1.5 (6) | C1—N1—C5—C4 | 0.9 (5) |
C8—C9—C10—C11 | −2.5 (6) | C5—N1—C1—C2 | −1.1 (5) |
C10—C11—C12—C7 | 1.5 (4) | C4—C3—C2—C1 | 0.8 (5) |
Symmetry code: (i) x−y, −y, −z+1. |
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