Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020836/ob2023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020836/ob2023Isup2.hkl |
CCDC reference: 613786
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.
C20H14N2O | F(000) = 312.00 |
Mr = 298.34 | Dx = 1.415 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P -2yc | Cell parameters from 1800 reflections |
a = 11.7365 (19) Å | θ = 3.5–27.5° |
b = 5.8687 (5) Å | µ = 0.09 mm−1 |
c = 14.251 (2) Å | T = 93 K |
β = 134.496 (4)° | Platelet, orange |
V = 700.15 (17) Å3 | 0.55 × 0.10 × 0.05 mm |
Z = 2 |
Rigaku Mercury diffractometer | 1610 independent reflections |
Detector resolution: 7.31 pixels mm-1 | 1521 reflections with F2 > 2σ(F2) |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −15→15 |
Tmin = 0.933, Tmax = 0.996 | k = −7→7 |
1610 measured reflections | l = −18→18 |
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0746P)2 + 0.0816P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.107 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.32 e Å−3 |
1610 reflections | Δρmin = −0.22 e Å−3 |
209 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4733 (2) | 0.5640 (2) | 0.58855 (16) | 0.0202 (3) | |
N1 | 0.4083 (2) | 0.8240 (3) | 0.40625 (17) | 0.0141 (3) | |
N2 | 0.2251 (2) | 1.0834 (3) | 0.41394 (18) | 0.0152 (3) | |
C1 | 0.5559 (2) | 0.4404 (3) | 0.5832 (2) | 0.0145 (4) | |
C2 | 0.6287 (2) | 0.2320 (3) | 0.6598 (2) | 0.0175 (4) | |
C3 | 0.7158 (2) | 0.0956 (3) | 0.6539 (2) | 0.0164 (4) | |
C4 | 0.7444 (2) | 0.1461 (3) | 0.57307 (19) | 0.0139 (4) | |
C5 | 0.8344 (2) | −0.0029 (4) | 0.5687 (2) | 0.0162 (4) | |
C6 | 0.8644 (2) | 0.0460 (4) | 0.4932 (2) | 0.0196 (4) | |
C7 | 0.8032 (2) | 0.2470 (3) | 0.4194 (2) | 0.0191 (4) | |
C8 | 0.7127 (2) | 0.3955 (3) | 0.4210 (2) | 0.0176 (4) | |
C9 | 0.6797 (2) | 0.3481 (3) | 0.49698 (19) | 0.0129 (4) | |
C10 | 0.5810 (2) | 0.4958 (3) | 0.4988 (2) | 0.0133 (4) | |
C11 | 0.5045 (2) | 0.6815 (3) | 0.4157 (2) | 0.0141 (4) | |
C12 | 0.3328 (2) | 1.0145 (3) | 0.3224 (2) | 0.0131 (4) | |
C13 | 0.3466 (2) | 1.0744 (3) | 0.2377 (2) | 0.0165 (4) | |
C14 | 0.2732 (2) | 1.2755 (3) | 0.1613 (2) | 0.0172 (4) | |
C15 | 0.1880 (2) | 1.4136 (3) | 0.1708 (2) | 0.0157 (4) | |
C16 | 0.1704 (2) | 1.3559 (3) | 0.2566 (2) | 0.0135 (4) | |
C17 | 0.0857 (2) | 1.4930 (4) | 0.2722 (2) | 0.0169 (4) | |
C18 | 0.0707 (2) | 1.4230 (3) | 0.3549 (2) | 0.0176 (4) | |
C19 | 0.1419 (2) | 1.2148 (3) | 0.4227 (2) | 0.0181 (4) | |
C20 | 0.2409 (2) | 1.1521 (3) | 0.33223 (19) | 0.0128 (4) | |
H1 | 0.3908 | 0.7985 | 0.4587 | 0.017* | |
H2 | 0.6053 | 0.1921 | 0.7123 | 0.021* | |
H3 | 0.7625 | −0.0549 | 0.7062 | 0.020* | |
H5 | 0.8762 | −0.1423 | 0.6236 | 0.019* | |
H6 | 0.9266 | −0.0488 | 0.4911 | 0.024* | |
H7 | 0.8235 | 0.2817 | 0.3652 | 0.023* | |
H8 | 0.6683 | 0.5310 | 0.3646 | 0.021* | |
H11 | 0.5158 | 0.7079 | 0.3543 | 0.017* | |
H13 | 0.4156 | 0.9734 | 0.2335 | 0.020* | |
H14 | 0.2938 | 1.3138 | 0.1105 | 0.021* | |
H15 | 0.1460 | 1.5585 | 0.1227 | 0.019* | |
H17 | 0.0378 | 1.6413 | 0.2228 | 0.020* | |
H18 | 0.0145 | 1.5151 | 0.3684 | 0.021* | |
H19 | 0.1298 | 1.1680 | 0.4802 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0220 (7) | 0.0222 (8) | 0.0222 (7) | 0.0020 (6) | 0.0176 (6) | −0.0005 (6) |
N1 | 0.0147 (7) | 0.0135 (7) | 0.0156 (8) | 0.0006 (6) | 0.0112 (7) | −0.0006 (6) |
N2 | 0.0145 (8) | 0.0161 (8) | 0.0157 (8) | −0.0006 (7) | 0.0108 (7) | −0.0013 (7) |
C1 | 0.0136 (9) | 0.0165 (9) | 0.0143 (9) | −0.0021 (8) | 0.0101 (8) | −0.0035 (8) |
C2 | 0.0189 (10) | 0.0203 (10) | 0.0146 (9) | −0.0016 (8) | 0.0122 (8) | 0.0009 (8) |
C3 | 0.0160 (9) | 0.0140 (10) | 0.0145 (9) | −0.0013 (8) | 0.0090 (8) | 0.0007 (8) |
C4 | 0.0121 (9) | 0.0117 (9) | 0.0143 (9) | −0.0015 (8) | 0.0080 (8) | −0.0009 (8) |
C5 | 0.0137 (10) | 0.0120 (9) | 0.0160 (10) | 0.0001 (7) | 0.0079 (9) | 0.0000 (7) |
C6 | 0.0156 (10) | 0.0199 (10) | 0.0224 (11) | 0.0005 (8) | 0.0130 (9) | −0.0045 (9) |
C7 | 0.0201 (10) | 0.0221 (11) | 0.0198 (10) | −0.0005 (8) | 0.0157 (9) | −0.0022 (8) |
C8 | 0.0190 (10) | 0.0195 (10) | 0.0180 (9) | 0.0009 (8) | 0.0143 (9) | 0.0015 (8) |
C9 | 0.0119 (9) | 0.0123 (9) | 0.0126 (9) | −0.0018 (7) | 0.0079 (8) | −0.0036 (8) |
C10 | 0.0136 (9) | 0.0146 (9) | 0.0137 (9) | −0.0013 (8) | 0.0103 (9) | −0.0019 (8) |
C11 | 0.0126 (8) | 0.0135 (9) | 0.0175 (9) | −0.0020 (7) | 0.0109 (8) | −0.0032 (8) |
C12 | 0.0116 (9) | 0.0100 (9) | 0.0142 (9) | −0.0013 (7) | 0.0077 (8) | −0.0012 (8) |
C13 | 0.0156 (9) | 0.0168 (10) | 0.0189 (10) | 0.0008 (8) | 0.0127 (9) | −0.0015 (8) |
C14 | 0.0153 (9) | 0.0213 (10) | 0.0168 (10) | −0.0002 (8) | 0.0119 (8) | 0.0012 (8) |
C15 | 0.0147 (9) | 0.0149 (10) | 0.0167 (10) | 0.0003 (7) | 0.0107 (9) | 0.0024 (8) |
C16 | 0.0110 (8) | 0.0120 (9) | 0.0138 (9) | −0.0022 (8) | 0.0073 (8) | −0.0032 (8) |
C17 | 0.0126 (9) | 0.0164 (10) | 0.0182 (10) | 0.0004 (7) | 0.0095 (9) | −0.0017 (8) |
C18 | 0.0160 (10) | 0.0189 (10) | 0.0197 (10) | 0.0004 (8) | 0.0131 (9) | −0.0034 (8) |
C19 | 0.0195 (10) | 0.0191 (10) | 0.0201 (10) | −0.0008 (8) | 0.0154 (9) | −0.0007 (8) |
C20 | 0.0118 (9) | 0.0127 (9) | 0.0132 (9) | −0.0004 (7) | 0.0085 (8) | 0.0003 (7) |
O1—C1 | 1.256 (3) | C14—C15 | 1.365 (4) |
N1—C11 | 1.334 (3) | C15—C16 | 1.416 (4) |
N1—C12 | 1.407 (2) | C16—C17 | 1.414 (4) |
N2—C19 | 1.317 (4) | C16—C20 | 1.424 (2) |
N2—C20 | 1.362 (4) | C17—C18 | 1.370 (5) |
C1—C2 | 1.453 (3) | C18—C19 | 1.412 (3) |
C1—C10 | 1.461 (5) | N1—H1 | 0.916 |
C2—C3 | 1.347 (4) | C2—H2 | 0.989 |
C3—C4 | 1.438 (4) | C3—H3 | 1.031 |
C4—C5 | 1.406 (4) | C5—H5 | 0.992 |
C4—C9 | 1.416 (2) | C6—H6 | 0.936 |
C5—C6 | 1.376 (5) | C7—H7 | 0.976 |
C6—C7 | 1.398 (3) | C8—H8 | 0.981 |
C7—C8 | 1.386 (4) | C11—H11 | 0.985 |
C8—C9 | 1.410 (4) | C13—H13 | 1.039 |
C9—C10 | 1.461 (4) | C14—H14 | 0.937 |
C10—C11 | 1.381 (2) | C15—H15 | 0.981 |
C12—C13 | 1.371 (4) | C17—H17 | 1.007 |
C12—C20 | 1.431 (4) | C18—H18 | 0.971 |
C13—C14 | 1.416 (3) | C19—H19 | 0.964 |
C11—N1—C12 | 124.6 (2) | N2—C19—C18 | 124.4 (3) |
C19—N2—C20 | 117.5 (2) | N2—C20—C12 | 118.7 (2) |
O1—C1—C2 | 120.8 (3) | N2—C20—C16 | 122.8 (2) |
O1—C1—C10 | 122.1 (2) | C12—C20—C16 | 118.5 (2) |
C2—C1—C10 | 117.0 (2) | C11—N1—H1 | 118.2 |
C1—C2—C3 | 121.7 (3) | C12—N1—H1 | 117.1 |
C2—C3—C4 | 122.8 (2) | C1—C2—H2 | 116.1 |
C3—C4—C5 | 120.8 (2) | C3—C2—H2 | 122.2 |
C3—C4—C9 | 119.0 (2) | C2—C3—H3 | 120.4 |
C5—C4—C9 | 120.2 (2) | C4—C3—H3 | 116.8 |
C4—C5—C6 | 121.1 (2) | C4—C5—H5 | 116.7 |
C5—C6—C7 | 119.1 (2) | C6—C5—H5 | 122.2 |
C6—C7—C8 | 120.9 (3) | C5—C6—H6 | 122.3 |
C7—C8—C9 | 121.0 (2) | C7—C6—H6 | 118.6 |
C4—C9—C8 | 117.7 (2) | C6—C7—H7 | 119.3 |
C4—C9—C10 | 119.3 (2) | C8—C7—H7 | 119.8 |
C8—C9—C10 | 123.0 (2) | C7—C8—H8 | 118.0 |
C1—C10—C9 | 120.13 (19) | C9—C8—H8 | 121.0 |
C1—C10—C11 | 119.8 (2) | N1—C11—H11 | 116.3 |
C9—C10—C11 | 120.0 (3) | C10—C11—H11 | 118.3 |
N1—C11—C10 | 125.3 (3) | C12—C13—H13 | 118.8 |
N1—C12—C13 | 124.0 (2) | C14—C13—H13 | 120.7 |
N1—C12—C20 | 115.7 (2) | C13—C14—H14 | 116.5 |
C13—C12—C20 | 120.23 (19) | C15—C14—H14 | 122.5 |
C12—C13—C14 | 120.5 (2) | C14—C15—H15 | 119.4 |
C13—C14—C15 | 120.8 (3) | C16—C15—H15 | 120.3 |
C14—C15—C16 | 120.2 (2) | C16—C17—H17 | 119.4 |
C15—C16—C17 | 123.0 (2) | C18—C17—H17 | 121.0 |
C15—C16—C20 | 119.8 (2) | C17—C18—H18 | 121.2 |
C17—C16—C20 | 117.2 (2) | C19—C18—H18 | 120.3 |
C16—C17—C18 | 119.6 (2) | N2—C19—H19 | 118.3 |
C17—C18—C19 | 118.5 (3) | C18—C19—H19 | 117.3 |
C11—N1—C12—C13 | 1.3 (2) | C7—C8—C9—C10 | −178.16 (16) |
C11—N1—C12—C20 | −176.89 (16) | C4—C9—C10—C1 | 2.8 (2) |
C12—N1—C11—C10 | 179.11 (17) | C4—C9—C10—C11 | −173.78 (16) |
C19—N2—C20—C12 | 179.03 (15) | C8—C9—C10—C1 | −177.99 (16) |
C19—N2—C20—C16 | −0.7 (2) | C8—C9—C10—C11 | 5.4 (2) |
C20—N2—C19—C18 | −1.1 (2) | C1—C10—C11—N1 | 1.4 (2) |
O1—C1—C2—C3 | 179.00 (17) | C9—C10—C11—N1 | 178.06 (16) |
O1—C1—C10—C9 | 179.32 (16) | N1—C12—C13—C14 | −176.76 (16) |
O1—C1—C10—C11 | −4.1 (2) | N1—C12—C20—N2 | −3.9 (2) |
C2—C1—C10—C9 | −1.8 (2) | N1—C12—C20—C16 | 175.76 (15) |
C2—C1—C10—C11 | 174.81 (16) | C13—C12—C20—N2 | 177.78 (16) |
C10—C1—C2—C3 | 0.1 (2) | C13—C12—C20—C16 | −2.5 (2) |
C1—C2—C3—C4 | 0.6 (2) | C20—C12—C13—C14 | 1.4 (2) |
C2—C3—C4—C5 | −179.18 (17) | C12—C13—C14—C15 | 0.3 (2) |
C2—C3—C4—C9 | 0.4 (2) | C13—C14—C15—C16 | −0.7 (2) |
C3—C4—C5—C6 | −178.98 (16) | C14—C15—C16—C17 | 179.13 (17) |
C3—C4—C9—C8 | 178.66 (15) | C14—C15—C16—C20 | −0.5 (2) |
C3—C4—C9—C10 | −2.1 (2) | C15—C16—C17—C18 | 178.51 (17) |
C5—C4—C9—C8 | −1.7 (2) | C15—C16—C20—N2 | −178.25 (16) |
C5—C4—C9—C10 | 177.50 (15) | C15—C16—C20—C12 | 2.1 (2) |
C9—C4—C5—C6 | 1.4 (2) | C17—C16—C20—N2 | 2.1 (2) |
C4—C5—C6—C7 | −0.3 (2) | C17—C16—C20—C12 | −177.56 (15) |
C5—C6—C7—C8 | −0.4 (2) | C20—C16—C17—C18 | −1.9 (2) |
C6—C7—C8—C9 | 0.0 (2) | C16—C17—C18—C19 | 0.3 (2) |
C7—C8—C9—C4 | 1.0 (2) | C17—C18—C19—N2 | 1.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.92 | 1.94 | 2.624 (3) | 131 |
N1—H1···N2 | 0.92 | 2.29 | 2.698 (3) | 107 |