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The structure of the title compound, C
32H
23BrN
2O
3·H
2O, is stabilized by intramolecular C—H
O interactions, and the molecular packing is stabilized by intermolecular C—H
O and N—H
N hydrogen bonds.
Supporting information
CCDC reference: 238797
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- H-atom completeness 93%
- R factor = 0.059
- wR factor = 0.174
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O38
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
PLAT430_ALERT_2_B Short Inter D...A Contact O35 .. O38 .. 2.75 Ang.
Alert level C
ABSTY02_ALERT_1_C An _exptl_absorpt_correction_type has been given without
a literature citation. This should be contained in the
_exptl_absorpt_process_details field.
Absorption correction given as multi-scan
WEIGH01_ALERT_1_C Extra text has been found in the
_refine_ls_weighting_scheme field. This should be in the
_refine_ls_weighting_details field.
Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0878P)^2^+0.2892
Weighting scheme identified as calc
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.66 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C33
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C18
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C32 H23 Br N2 O3
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C32 H25 Br1 N2 O4
Atom count from the _atom_site data: C32 H23 Br1 N2 O4
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C32 H25 Br N2 O4
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 128.00 128.00 0.00
H 100.00 92.00 8.00
Br 4.00 4.00 0.00
N 8.00 8.00 0.00
O 16.00 16.00 0.00
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
2'-(4-Bromobenzoyl)acenaphthene-1-spiro-3'-pyrrolizidine-1'-spiro-3''-
indole-2,2''(1
H,3''H)-dione monohydrate
top
Crystal data top
C32H23BrN2O3·H2O | F(000) = 1184 |
Mr = 581.45 | Dx = 1.457 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4878 (8) Å | Cell parameters from 2395 reflections |
b = 22.4857 (18) Å | θ = 2.4–20.5° |
c = 12.6805 (10) Å | µ = 1.59 mm−1 |
β = 101.500 (2)° | T = 293 K |
V = 2650.9 (4) Å3 | Block, colourless |
Z = 4 | 0.21 × 0.20 × 0.20 mm |
Data collection top
CCD Area Detector diffractometer | 5843 independent reflections |
Radiation source: fine-focus sealed tube | 3094 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω scans | θmax = 28.0°, θmin = 1.8° |
Absorption correction: multi-scan | h = −12→10 |
Tmin = 0.731, Tmax = 0.741 | k = −28→29 |
15993 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 0.99 | Calculated w = 1/[σ2(Fo2) + (0.0878P)2 + 0.2892P] where P = (Fo2 + 2Fc2)/3 |
5843 reflections | (Δ/σ)max < 0.001 |
352 parameters | Δρmax = 0.75 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | −0.00559 (6) | 0.02823 (2) | 0.78181 (4) | 0.1023 (3) | |
N1 | −0.4054 (3) | −0.22613 (11) | 0.2159 (2) | 0.0412 (6) | |
C2 | −0.3809 (4) | −0.16132 (13) | 0.2121 (2) | 0.0419 (8) | |
C3 | −0.2892 (4) | −0.14477 (12) | 0.3231 (2) | 0.0382 (7) | |
H3 | −0.1885 | −0.1471 | 0.3155 | 0.046* | |
C4 | −0.3107 (3) | −0.19506 (13) | 0.4030 (2) | 0.0366 (7) | |
C5 | −0.4150 (4) | −0.23921 (13) | 0.3273 (2) | 0.0424 (8) | |
H5 | −0.5138 | −0.2317 | 0.3360 | 0.051* | |
C6 | −0.1661 (4) | −0.22352 (13) | 0.4547 (2) | 0.0419 (8) | |
N7 | −0.1626 (3) | −0.22977 (12) | 0.5610 (2) | 0.0475 (7) | |
H7 | −0.0949 | −0.2476 | 0.6049 | 0.057* | |
C8 | −0.2819 (4) | −0.20395 (14) | 0.5911 (3) | 0.0442 (8) | |
C9 | −0.3162 (5) | −0.20091 (18) | 0.6910 (3) | 0.0616 (10) | |
H9 | −0.2568 | −0.2179 | 0.7507 | 0.074* | |
C10 | −0.4410 (5) | −0.17208 (19) | 0.7005 (3) | 0.0723 (12) | |
H10 | −0.4661 | −0.1696 | 0.7677 | 0.087* | |
C11 | −0.5296 (5) | −0.14693 (18) | 0.6126 (3) | 0.0686 (12) | |
H11 | −0.6116 | −0.1265 | 0.6214 | 0.082* | |
C12 | −0.4971 (4) | −0.15190 (15) | 0.5109 (3) | 0.0537 (9) | |
H12 | −0.5589 | −0.1364 | 0.4510 | 0.064* | |
C13 | −0.3718 (4) | −0.18014 (13) | 0.5004 (2) | 0.0414 (8) | |
C14 | −0.3136 (4) | −0.08113 (14) | 0.3550 (3) | 0.0451 (8) | |
C15 | −0.2332 (4) | −0.05670 (13) | 0.4593 (3) | 0.0425 (8) | |
C16 | −0.2977 (4) | −0.01047 (16) | 0.5053 (3) | 0.0570 (10) | |
H16 | −0.3860 | 0.0043 | 0.4697 | 0.068* | |
C17 | −0.2335 (5) | 0.01375 (17) | 0.6021 (3) | 0.0665 (11) | |
H17 | −0.2793 | 0.0433 | 0.6342 | 0.080* | |
C18 | −0.0990 (5) | −0.00671 (17) | 0.6511 (3) | 0.0595 (10) | |
C19 | −0.0294 (5) | −0.05037 (15) | 0.6046 (3) | 0.0608 (10) | |
H19 | 0.0630 | −0.0623 | 0.6367 | 0.073* | |
C20 | −0.0992 (4) | −0.07602 (14) | 0.5097 (3) | 0.0526 (9) | |
H20 | −0.0551 | −0.1068 | 0.4793 | 0.063* | |
C21 | −0.3179 (4) | −0.14072 (14) | 0.1160 (2) | 0.0492 (9) | |
C22 | −0.1832 (5) | −0.14545 (17) | 0.0945 (3) | 0.0619 (11) | |
H22 | −0.1103 | −0.1651 | 0.1416 | 0.074* | |
C23 | −0.1576 (6) | −0.1196 (2) | −0.0011 (3) | 0.0805 (14) | |
H23 | −0.0661 | −0.1229 | −0.0165 | 0.097* | |
C24 | −0.2589 (8) | −0.0906 (2) | −0.0709 (4) | 0.0903 (17) | |
H24 | −0.2361 | −0.0743 | −0.1328 | 0.108* | |
C25 | −0.4003 (6) | −0.08443 (16) | −0.0517 (3) | 0.0726 (14) | |
C26 | −0.5188 (8) | −0.05470 (19) | −0.1127 (4) | 0.096 (2) | |
H26 | −0.5094 | −0.0372 | −0.1773 | 0.116* | |
C27 | −0.6464 (8) | −0.05056 (19) | −0.0808 (4) | 0.097 (2) | |
H27 | −0.7221 | −0.0308 | −0.1247 | 0.117* | |
C28 | −0.6685 (6) | −0.07556 (17) | 0.0178 (4) | 0.0825 (15) | |
H28 | −0.7559 | −0.0719 | 0.0398 | 0.099* | |
C29 | −0.5539 (5) | −0.10552 (14) | 0.0790 (3) | 0.0577 (10) | |
C30 | −0.4245 (5) | −0.11023 (14) | 0.0449 (3) | 0.0550 (10) | |
C31 | −0.5351 (4) | −0.13413 (15) | 0.1853 (3) | 0.0513 (9) | |
C32 | −0.2930 (4) | −0.26575 (15) | 0.1902 (3) | 0.0526 (9) | |
H32A | −0.1976 | −0.2501 | 0.2186 | 0.063* | |
H32B | −0.3042 | −0.2714 | 0.1132 | 0.063* | |
C33 | −0.3188 (6) | −0.32291 (17) | 0.2456 (4) | 0.0767 (13) | |
H33A | −0.2289 | −0.3440 | 0.2698 | 0.092* | |
H33B | −0.3838 | −0.3485 | 0.1968 | 0.092* | |
C34 | −0.3848 (4) | −0.30556 (14) | 0.3408 (3) | 0.0541 (9) | |
H34A | −0.3184 | −0.3135 | 0.4080 | 0.065* | |
H34B | −0.4730 | −0.3275 | 0.3400 | 0.065* | |
O35 | −0.0705 (3) | −0.23839 (11) | 0.40883 (19) | 0.0565 (6) | |
O36 | −0.3989 (3) | −0.04994 (11) | 0.2957 (2) | 0.0709 (8) | |
O37 | −0.6244 (3) | −0.14059 (13) | 0.2410 (2) | 0.0754 (8) | |
O38 | 0.8667 (10) | 0.1615 (4) | 0.6388 (10) | 0.320 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0989 (5) | 0.1098 (5) | 0.0820 (4) | −0.0040 (3) | −0.0206 (3) | −0.0411 (3) |
N1 | 0.0418 (17) | 0.0399 (14) | 0.0392 (14) | 0.0002 (13) | 0.0013 (12) | −0.0015 (11) |
C2 | 0.044 (2) | 0.0409 (17) | 0.0377 (17) | 0.0015 (15) | 0.0003 (15) | 0.0032 (13) |
C3 | 0.041 (2) | 0.0387 (16) | 0.0335 (15) | 0.0040 (14) | 0.0034 (14) | 0.0010 (12) |
C4 | 0.037 (2) | 0.0363 (15) | 0.0353 (16) | 0.0042 (14) | 0.0052 (14) | 0.0036 (12) |
C5 | 0.042 (2) | 0.0438 (18) | 0.0396 (17) | −0.0046 (15) | 0.0045 (15) | 0.0014 (13) |
C6 | 0.041 (2) | 0.0408 (17) | 0.0412 (18) | 0.0004 (16) | 0.0010 (16) | 0.0003 (14) |
N7 | 0.0471 (19) | 0.0556 (17) | 0.0358 (14) | 0.0084 (14) | −0.0011 (13) | 0.0083 (12) |
C8 | 0.047 (2) | 0.0460 (18) | 0.0384 (18) | −0.0057 (16) | 0.0046 (16) | −0.0009 (14) |
C9 | 0.060 (3) | 0.087 (3) | 0.0363 (19) | −0.009 (2) | 0.0055 (19) | −0.0021 (18) |
C10 | 0.084 (3) | 0.092 (3) | 0.046 (2) | −0.017 (3) | 0.025 (2) | −0.018 (2) |
C11 | 0.072 (3) | 0.072 (3) | 0.071 (3) | 0.002 (2) | 0.035 (3) | −0.011 (2) |
C12 | 0.048 (2) | 0.056 (2) | 0.058 (2) | 0.0036 (18) | 0.0128 (19) | 0.0053 (17) |
C13 | 0.045 (2) | 0.0384 (16) | 0.0408 (18) | −0.0020 (15) | 0.0086 (16) | 0.0005 (13) |
C14 | 0.053 (2) | 0.0429 (18) | 0.0371 (17) | −0.0004 (16) | 0.0045 (16) | 0.0046 (14) |
C15 | 0.045 (2) | 0.0365 (17) | 0.0439 (18) | 0.0006 (16) | 0.0051 (16) | 0.0021 (14) |
C16 | 0.045 (2) | 0.059 (2) | 0.063 (2) | 0.0036 (18) | 0.0028 (19) | −0.0098 (18) |
C17 | 0.060 (3) | 0.064 (2) | 0.073 (3) | 0.001 (2) | 0.009 (2) | −0.027 (2) |
C18 | 0.063 (3) | 0.054 (2) | 0.055 (2) | −0.007 (2) | −0.004 (2) | −0.0096 (17) |
C19 | 0.057 (3) | 0.0401 (19) | 0.074 (3) | −0.0010 (18) | −0.016 (2) | −0.0001 (18) |
C20 | 0.052 (3) | 0.0356 (17) | 0.066 (2) | 0.0023 (17) | 0.0019 (19) | −0.0043 (15) |
C21 | 0.067 (3) | 0.0439 (18) | 0.0326 (17) | −0.0073 (17) | 0.0007 (17) | −0.0011 (13) |
C22 | 0.071 (3) | 0.072 (3) | 0.045 (2) | −0.014 (2) | 0.018 (2) | −0.0092 (17) |
C23 | 0.104 (4) | 0.088 (3) | 0.056 (3) | −0.023 (3) | 0.031 (3) | −0.011 (2) |
C24 | 0.162 (6) | 0.067 (3) | 0.049 (3) | −0.035 (3) | 0.038 (3) | −0.006 (2) |
C25 | 0.136 (5) | 0.039 (2) | 0.033 (2) | −0.011 (2) | −0.005 (2) | −0.0021 (15) |
C26 | 0.183 (7) | 0.044 (2) | 0.046 (2) | 0.002 (3) | −0.015 (3) | 0.0060 (18) |
C27 | 0.151 (6) | 0.046 (2) | 0.064 (3) | 0.023 (3) | −0.051 (3) | −0.001 (2) |
C28 | 0.104 (4) | 0.051 (2) | 0.071 (3) | 0.019 (2) | −0.034 (3) | −0.007 (2) |
C29 | 0.073 (3) | 0.0362 (18) | 0.051 (2) | 0.0033 (19) | −0.018 (2) | −0.0018 (15) |
C30 | 0.084 (3) | 0.0382 (18) | 0.0360 (18) | −0.0056 (19) | −0.0035 (19) | −0.0009 (14) |
C31 | 0.051 (3) | 0.0462 (19) | 0.051 (2) | −0.0002 (17) | −0.0044 (18) | −0.0017 (16) |
C32 | 0.064 (3) | 0.051 (2) | 0.0416 (18) | 0.0069 (18) | 0.0067 (17) | −0.0054 (15) |
C33 | 0.102 (4) | 0.049 (2) | 0.083 (3) | 0.003 (2) | 0.031 (3) | −0.001 (2) |
C34 | 0.059 (3) | 0.0437 (19) | 0.056 (2) | −0.0079 (18) | 0.0031 (19) | 0.0042 (16) |
O35 | 0.0467 (16) | 0.0707 (16) | 0.0521 (14) | 0.0140 (13) | 0.0096 (13) | 0.0016 (12) |
O36 | 0.096 (2) | 0.0499 (14) | 0.0532 (15) | 0.0234 (15) | −0.0167 (15) | 0.0013 (12) |
O37 | 0.0535 (19) | 0.087 (2) | 0.083 (2) | 0.0174 (15) | 0.0070 (17) | 0.0128 (16) |
O38 | 0.290 (10) | 0.224 (8) | 0.496 (15) | −0.073 (7) | 0.197 (10) | −0.091 (9) |
Geometric parameters (Å, º) top
Br1—C18 | 1.888 (4) | C16—H16 | 0.9300 |
N1—C5 | 1.462 (4) | C17—C18 | 1.382 (6) |
N1—C32 | 1.475 (4) | C17—H17 | 0.9300 |
N1—C2 | 1.478 (4) | C18—C19 | 1.379 (5) |
C2—C21 | 1.533 (5) | C19—C20 | 1.379 (5) |
C2—C3 | 1.545 (4) | C19—H19 | 0.9300 |
C2—C31 | 1.559 (5) | C20—H20 | 0.9300 |
C3—C14 | 1.518 (4) | C21—C22 | 1.363 (5) |
C3—C4 | 1.559 (4) | C21—C30 | 1.393 (5) |
C3—H3 | 0.9800 | C22—C23 | 1.409 (6) |
C4—C13 | 1.504 (4) | C22—H22 | 0.9300 |
C4—C6 | 1.537 (4) | C23—C24 | 1.339 (7) |
C4—C5 | 1.584 (4) | C23—H23 | 0.9300 |
C5—C34 | 1.522 (4) | C24—C25 | 1.417 (7) |
C5—H5 | 0.9800 | C24—H24 | 0.9300 |
C6—O35 | 1.218 (4) | C25—C26 | 1.401 (7) |
C6—N7 | 1.350 (4) | C25—C30 | 1.415 (5) |
N7—C8 | 1.391 (4) | C26—C27 | 1.354 (7) |
N7—H7 | 0.8600 | C26—H26 | 0.9300 |
C8—C9 | 1.372 (5) | C27—C28 | 1.424 (7) |
C8—C13 | 1.395 (4) | C27—H27 | 0.9300 |
C9—C10 | 1.377 (6) | C28—C29 | 1.379 (5) |
C9—H9 | 0.9300 | C28—H28 | 0.9300 |
C10—C11 | 1.377 (6) | C29—C30 | 1.385 (6) |
C10—H10 | 0.9300 | C29—C31 | 1.472 (5) |
C11—C12 | 1.388 (5) | C31—O37 | 1.215 (4) |
C11—H11 | 0.9300 | C32—C33 | 1.508 (5) |
C12—C13 | 1.378 (5) | C32—H32A | 0.9700 |
C12—H12 | 0.9300 | C32—H32B | 0.9700 |
C14—O36 | 1.212 (4) | C33—C34 | 1.517 (5) |
C14—C15 | 1.493 (4) | C33—H33A | 0.9700 |
C15—C20 | 1.375 (5) | C33—H33B | 0.9700 |
C15—C16 | 1.392 (5) | C34—H34A | 0.9700 |
C16—C17 | 1.370 (5) | C34—H34B | 0.9700 |
| | | |
C5—N1—C32 | 106.2 (2) | C18—C17—H17 | 120.8 |
C5—N1—C2 | 105.7 (2) | C19—C18—C17 | 121.5 (3) |
C32—N1—C2 | 117.6 (3) | C19—C18—Br1 | 119.4 (3) |
N1—C2—C21 | 114.4 (2) | C17—C18—Br1 | 119.1 (3) |
N1—C2—C3 | 105.8 (2) | C18—C19—C20 | 118.9 (4) |
C21—C2—C3 | 114.4 (3) | C18—C19—H19 | 120.6 |
N1—C2—C31 | 104.3 (3) | C20—C19—H19 | 120.6 |
C21—C2—C31 | 101.9 (3) | C15—C20—C19 | 120.8 (3) |
C3—C2—C31 | 116.0 (3) | C15—C20—H20 | 119.6 |
C14—C3—C2 | 112.5 (3) | C19—C20—H20 | 119.6 |
C14—C3—C4 | 117.6 (2) | C22—C21—C30 | 119.9 (3) |
C2—C3—C4 | 107.1 (2) | C22—C21—C2 | 131.7 (3) |
C14—C3—H3 | 106.3 | C30—C21—C2 | 108.4 (3) |
C2—C3—H3 | 106.3 | C21—C22—C23 | 118.0 (4) |
C4—C3—H3 | 106.3 | C21—C22—H22 | 121.0 |
C13—C4—C6 | 101.5 (2) | C23—C22—H22 | 121.0 |
C13—C4—C3 | 119.6 (2) | C24—C23—C22 | 123.1 (5) |
C6—C4—C3 | 111.0 (3) | C24—C23—H23 | 118.4 |
C13—C4—C5 | 110.0 (3) | C22—C23—H23 | 118.4 |
C6—C4—C5 | 113.2 (2) | C23—C24—C25 | 120.8 (4) |
C3—C4—C5 | 102.0 (2) | C23—C24—H24 | 119.6 |
N1—C5—C34 | 105.0 (3) | C25—C24—H24 | 119.6 |
N1—C5—C4 | 107.9 (2) | C26—C25—C30 | 115.0 (5) |
C34—C5—C4 | 117.7 (3) | C26—C25—C24 | 129.4 (5) |
N1—C5—H5 | 108.6 | C30—C25—C24 | 115.6 (4) |
C34—C5—H5 | 108.6 | C27—C26—C25 | 122.4 (5) |
C4—C5—H5 | 108.6 | C27—C26—H26 | 118.8 |
O35—C6—N7 | 125.2 (3) | C25—C26—H26 | 118.8 |
O35—C6—C4 | 126.7 (3) | C26—C27—C28 | 122.1 (5) |
N7—C6—C4 | 108.1 (3) | C26—C27—H27 | 118.9 |
C6—N7—C8 | 111.8 (3) | C28—C27—H27 | 118.9 |
C6—N7—H7 | 124.1 | C29—C28—C27 | 116.7 (5) |
C8—N7—H7 | 124.1 | C29—C28—H28 | 121.7 |
C9—C8—N7 | 129.0 (3) | C27—C28—H28 | 121.7 |
C9—C8—C13 | 121.6 (3) | C28—C29—C30 | 120.7 (4) |
N7—C8—C13 | 109.4 (3) | C28—C29—C31 | 131.8 (5) |
C8—C9—C10 | 118.1 (4) | C30—C29—C31 | 107.4 (3) |
C8—C9—H9 | 120.9 | C29—C30—C21 | 114.2 (3) |
C10—C9—H9 | 120.9 | C29—C30—C25 | 123.1 (4) |
C9—C10—C11 | 121.3 (4) | C21—C30—C25 | 122.7 (4) |
C9—C10—H10 | 119.4 | O37—C31—C29 | 127.8 (4) |
C11—C10—H10 | 119.4 | O37—C31—C2 | 124.0 (3) |
C10—C11—C12 | 120.5 (4) | C29—C31—C2 | 108.0 (3) |
C10—C11—H11 | 119.8 | N1—C32—C33 | 102.7 (3) |
C12—C11—H11 | 119.8 | N1—C32—H32A | 111.2 |
C13—C12—C11 | 118.8 (4) | C33—C32—H32A | 111.2 |
C13—C12—H12 | 120.6 | N1—C32—H32B | 111.2 |
C11—C12—H12 | 120.6 | C33—C32—H32B | 111.2 |
C12—C13—C8 | 119.7 (3) | H32A—C32—H32B | 109.1 |
C12—C13—C4 | 131.6 (3) | C32—C33—C34 | 106.4 (3) |
C8—C13—C4 | 108.6 (3) | C32—C33—H33A | 110.5 |
O36—C14—C15 | 119.7 (3) | C34—C33—H33A | 110.5 |
O36—C14—C3 | 119.9 (3) | C32—C33—H33B | 110.5 |
C15—C14—C3 | 120.3 (3) | C34—C33—H33B | 110.5 |
C20—C15—C16 | 118.9 (3) | H33A—C33—H33B | 108.6 |
C20—C15—C14 | 123.8 (3) | C33—C34—C5 | 105.1 (3) |
C16—C15—C14 | 117.2 (3) | C33—C34—H34A | 110.7 |
C17—C16—C15 | 121.3 (4) | C5—C34—H34A | 110.7 |
C17—C16—H16 | 119.4 | C33—C34—H34B | 110.7 |
C15—C16—H16 | 119.4 | C5—C34—H34B | 110.7 |
C16—C17—C18 | 118.4 (4) | H34A—C34—H34B | 108.8 |
C16—C17—H17 | 120.8 | | |
| | | |
C5—N1—C2—C21 | 160.4 (3) | C3—C14—C15—C20 | 28.2 (5) |
C32—N1—C2—C21 | 42.2 (4) | O36—C14—C15—C16 | 26.1 (5) |
C5—N1—C2—C3 | 33.6 (3) | C3—C14—C15—C16 | −153.8 (3) |
C32—N1—C2—C3 | −84.6 (3) | C20—C15—C16—C17 | −3.5 (6) |
C5—N1—C2—C31 | −89.2 (3) | C14—C15—C16—C17 | 178.4 (3) |
C32—N1—C2—C31 | 152.6 (3) | C15—C16—C17—C18 | 3.2 (6) |
N1—C2—C3—C14 | −151.8 (3) | C16—C17—C18—C19 | 0.1 (6) |
C21—C2—C3—C14 | 81.4 (3) | C16—C17—C18—Br1 | 177.6 (3) |
C31—C2—C3—C14 | −36.8 (4) | C17—C18—C19—C20 | −3.2 (6) |
N1—C2—C3—C4 | −21.1 (3) | Br1—C18—C19—C20 | 179.3 (3) |
C21—C2—C3—C4 | −147.9 (3) | C16—C15—C20—C19 | 0.3 (5) |
C31—C2—C3—C4 | 93.9 (3) | C14—C15—C20—C19 | 178.3 (3) |
C14—C3—C4—C13 | 7.6 (4) | C18—C19—C20—C15 | 2.9 (6) |
C2—C3—C4—C13 | −120.1 (3) | N1—C2—C21—C22 | −74.2 (5) |
C14—C3—C4—C6 | −110.1 (3) | C3—C2—C21—C22 | 48.0 (5) |
C2—C3—C4—C6 | 122.2 (3) | C31—C2—C21—C22 | 173.9 (3) |
C14—C3—C4—C5 | 129.1 (3) | N1—C2—C21—C30 | 108.7 (3) |
C2—C3—C4—C5 | 1.4 (3) | C3—C2—C21—C30 | −129.1 (3) |
C32—N1—C5—C34 | −34.2 (3) | C31—C2—C21—C30 | −3.1 (3) |
C2—N1—C5—C34 | −159.8 (3) | C30—C21—C22—C23 | −1.0 (5) |
C32—N1—C5—C4 | 92.2 (3) | C2—C21—C22—C23 | −177.8 (3) |
C2—N1—C5—C4 | −33.4 (3) | C21—C22—C23—C24 | 0.4 (6) |
C13—C4—C5—N1 | 147.2 (3) | C22—C23—C24—C25 | −0.2 (7) |
C6—C4—C5—N1 | −100.0 (3) | C23—C24—C25—C26 | 178.1 (4) |
C3—C4—C5—N1 | 19.2 (3) | C23—C24—C25—C30 | 0.5 (6) |
C13—C4—C5—C34 | −94.3 (3) | C30—C25—C26—C27 | 0.6 (6) |
C6—C4—C5—C34 | 18.5 (4) | C24—C25—C26—C27 | −177.0 (4) |
C3—C4—C5—C34 | 137.8 (3) | C25—C26—C27—C28 | 0.8 (8) |
C13—C4—C6—O35 | −173.0 (3) | C26—C27—C28—C29 | −1.3 (7) |
C3—C4—C6—O35 | −44.8 (4) | C27—C28—C29—C30 | 0.3 (5) |
C5—C4—C6—O35 | 69.1 (4) | C27—C28—C29—C31 | 176.9 (4) |
C13—C4—C6—N7 | 7.3 (3) | C28—C29—C30—C21 | 178.8 (3) |
C3—C4—C6—N7 | 135.6 (3) | C31—C29—C30—C21 | 1.5 (4) |
C5—C4—C6—N7 | −110.5 (3) | C28—C29—C30—C25 | 1.1 (5) |
O35—C6—N7—C8 | 174.7 (3) | C31—C29—C30—C25 | −176.2 (3) |
C4—C6—N7—C8 | −5.6 (4) | C22—C21—C30—C29 | −176.3 (3) |
C6—N7—C8—C9 | −179.7 (3) | C2—C21—C30—C29 | 1.2 (4) |
C6—N7—C8—C13 | 1.3 (4) | C22—C21—C30—C25 | 1.4 (5) |
N7—C8—C9—C10 | 179.3 (3) | C2—C21—C30—C25 | 178.9 (3) |
C13—C8—C9—C10 | −1.7 (5) | C26—C25—C30—C29 | −1.6 (5) |
C8—C9—C10—C11 | 0.0 (6) | C24—C25—C30—C29 | 176.3 (3) |
C9—C10—C11—C12 | 2.3 (6) | C26—C25—C30—C21 | −179.1 (3) |
C10—C11—C12—C13 | −2.8 (6) | C24—C25—C30—C21 | −1.1 (5) |
C11—C12—C13—C8 | 1.2 (5) | C28—C29—C31—O37 | 5.0 (6) |
C11—C12—C13—C4 | 176.7 (3) | C30—C29—C31—O37 | −178.1 (4) |
C9—C8—C13—C12 | 1.1 (5) | C28—C29—C31—C2 | 179.6 (4) |
N7—C8—C13—C12 | −179.7 (3) | C30—C29—C31—C2 | −3.5 (4) |
C9—C8—C13—C4 | −175.3 (3) | N1—C2—C31—O37 | 59.5 (4) |
N7—C8—C13—C4 | 3.8 (4) | C21—C2—C31—O37 | 178.8 (3) |
C6—C4—C13—C12 | 177.5 (3) | C3—C2—C31—O37 | −56.3 (4) |
C3—C4—C13—C12 | 55.1 (5) | N1—C2—C31—C29 | −115.3 (3) |
C5—C4—C13—C12 | −62.3 (4) | C21—C2—C31—C29 | 4.0 (3) |
C6—C4—C13—C8 | −6.6 (3) | C3—C2—C31—C29 | 128.9 (3) |
C3—C4—C13—C8 | −129.0 (3) | C5—N1—C32—C33 | 38.9 (3) |
C5—C4—C13—C8 | 113.5 (3) | C2—N1—C32—C33 | 156.8 (3) |
C2—C3—C14—O36 | 0.7 (4) | N1—C32—C33—C34 | −28.3 (4) |
C4—C3—C14—O36 | −124.4 (3) | C32—C33—C34—C5 | 8.1 (5) |
C2—C3—C14—C15 | −179.4 (3) | N1—C5—C34—C33 | 15.5 (4) |
C4—C3—C14—C15 | 55.5 (4) | C4—C5—C34—C33 | −104.6 (4) |
O36—C14—C15—C20 | −151.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O35 | 0.98 | 2.52 | 3.003 (4) | 110 |
C5—H5···O37 | 0.98 | 2.50 | 3.032 (4) | 113 |
C32—H32A···O35 | 0.97 | 2.49 | 3.191 (4) | 129 |
N7—H7···N1i | 0.86 | 2.13 | 2.980 (4) | 168 |
C26—H26···O36ii | 0.93 | 2.52 | 3.288 (5) | 140 |
Symmetry codes: (i) x+1/2, −y−1/2, z+1/2; (ii) −x−1, −y, −z. |
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