Di­bromo­phakellin methanol hemisolvate

Xu, S.-H.; Liao, X.-J.; Zeng, X.-C.; Yang, K.; He, D.-H.; Yu, K.-B.

doi:10.1107/S1600536804006622

Dibromophakellin methanol hemisolvate

S.-H. Xu, X.-J. Liao, X.-C. Zeng, K. Yang, D.-H. He and K.-B. Yu

The title compound, C₁₁H₁₁Br₂N₅O·0.5CH₃OH, was isolated from algae (Laurencia majuscula Lucas) collected from the South China Sea and its crystal structure was determined. It exhibits mild antibacterial and antineoplastic activity. The crystal structure has supramolecular layers with N—H

O and N—H

N hydrogen bonds. The methanol solvent molecule is threefold disordered.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006622/cf6316sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006622/cf6316Isup2.hkl Contains datablock I

CCDC reference: 239149

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.012 Å
Disorder in solvent or counterion
R factor = 0.037
wR factor = 0.067
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT214_ALERT_2_A Atom C12     (Anion/Solvent) ADP max/min Ratio         7.70 oblate
PLAT214_ALERT_2_A Atom C12'    (Anion/Solvent) ADP max/min Ratio         7.70 oblate
PLAT214_ALERT_2_A Atom C12"    (Anion/Solvent) ADP max/min Ratio         7.70 oblate
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.09 Ratio

Alert level B
PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor ....       6.93
PLAT731_ALERT_1_B Bond    Calc     0.86(5), Rep   0.856(10) ......       5.00 su-Rat
              N3   -H3N     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.86(6), Rep   0.855(10) ......       6.00 su-Rat
              N3'  -H3N'    1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.86(5), Rep   0.856(10) ......       5.00 su-Rat
              N3   -H3N     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.86(6), Rep   0.855(10) ......       6.00 su-Rat
              N3'  -H11#    1.555   1.555

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.14 Ratio
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors ....        C12
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors ....       C12'
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors ....       C12"
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        O2'
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT432_ALERT_2_C Short Inter X...Y Contact  Br2    ..  C5'     ..       3.30 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C1'    ..  O2'     ..       2.96 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         11
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.01

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:C11.5 H13 Br2 N5 O1.5
            Atom count from the _atom_site data:  C11.495 H12.98 Br2 N5 O1.495
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C11.50 H13 Br2 N5 O1.50
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         46.00     45.98    0.02
           H         52.00     51.92    0.08
           Br         8.00      8.00    0.00
           N         20.00     20.00    0.00
           O          6.00      5.98    0.02
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.49
           From the CIF: _reflns_number_total               5939
           Count of symmetry unique reflns         3061
           Completeness (_total/calc)            194.02%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2878
           Fraction of Friedel pairs measured     0.940
           Are heavy atom types Z>Si present          yes

   4 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
  17 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

  11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Dibromophakellin methanol hemisolvate top

Crystal data top

C₁₁H₁₁Br₂N₅O·0.5CH₄O	F(000) = 796
M_r = 405.09	D_x = 1.864 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.646 (1) Å	Cell parameters from 38 reflections
b = 28.050 (6) Å	θ = 3.0–15.3°
c = 7.670 (1) Å	µ = 5.62 mm⁻¹
β = 118.65 (1)°	T = 296 K
V = 1443.5 (5) Å³	Irregular, colourless
Z = 4	0.48 × 0.30 × 0.22 mm

Data collection top

Siemens P4 diffractometer	3078 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 26.5°, θ_min = 1.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SHELXTL; Siemens, 1994)	k = −35→35
T_min = 0.104, T_max = 0.290	l = −9→8
6923 measured reflections	3 standard reflections every 97 reflections
5939 independent reflections	intensity decay: 7.6%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.023P)²] where P = (F_o² + 2F_c²)/3
S = 0.80	(Δ/σ)_max = 0.001
5939 reflections	Δρ_max = 0.29 e Å⁻³
393 parameters	Δρ_min = −0.43 e Å⁻³
6 restraints	Absolute structure: Flack (1983); 2877 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (11)

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	U_iso*/U_eq	Occ. (<1)
Br1	0.07477 (12)	0.31318 (3)	0.15611 (12)	0.0632 (2)
Br2	0.53599 (13)	0.31463 (3)	0.61841 (11)	0.0643 (3)
O1	0.5937 (7)	0.4200 (2)	−0.0777 (7)	0.0585 (17)
N1	0.6139 (8)	0.37401 (19)	0.3654 (8)	0.0336 (14)
N2	0.8398 (9)	0.4254 (2)	0.2423 (8)	0.0393 (15)
N3	0.7876 (9)	0.4169 (2)	0.6741 (8)	0.0407 (15)
N4	0.8379 (8)	0.47357 (18)	0.4973 (7)	0.0369 (14)
N5	0.7163 (9)	0.4963 (2)	0.7097 (8)	0.0536 (18)
H5AN	0.7132	0.5259	0.6799	0.064*
H5BN	0.6788	0.4875	0.7941	0.064*
C1	0.6538 (12)	0.4136 (3)	0.1039 (11)	0.039 (2)
C2	0.5297 (12)	0.3891 (3)	0.1706 (11)	0.042 (2)
C3	0.3436 (12)	0.3725 (3)	0.0720 (12)	0.049 (2)
H3	0.2539	0.3777	−0.0612	0.059*
C4	0.3084 (11)	0.3458 (3)	0.2048 (11)	0.045 (2)
C5	0.4696 (12)	0.3471 (2)	0.3814 (11)	0.0372 (19)
C6	0.8073 (10)	0.3908 (2)	0.5273 (9)	0.0344 (17)
H6	0.8990	0.3640	0.5871	0.041*
C7	0.8977 (10)	0.4278 (2)	0.4500 (10)	0.0372 (17)
C8	1.1223 (11)	0.4253 (3)	0.5398 (11)	0.054 (3)
H8A	1.1667	0.3926	0.5488	0.064*
H8B	1.1874	0.4394	0.6713	0.064*
C9	1.1667 (11)	0.4543 (3)	0.3933 (10)	0.055 (2)
H9A	1.1869	0.4877	0.4304	0.067*
H9B	1.2850	0.4422	0.3921	0.067*
C10	0.9877 (10)	0.4480 (3)	0.1949 (10)	0.050 (2)
H10A	0.9396	0.4785	0.1294	0.060*
H10B	1.0171	0.4276	0.1102	0.060*
C11	0.7790 (10)	0.4639 (2)	0.6250 (9)	0.0350 (17)
Br1'	0.14905 (11)	0.25068 (3)	0.74252 (11)	0.0551 (2)
Br2'	0.63555 (13)	0.25818 (3)	1.18084 (12)	0.0694 (3)
O1'	0.8413 (8)	0.1505 (2)	0.6499 (8)	0.0605 (17)
N1'	0.3979 (8)	0.19561 (18)	0.6430 (9)	0.0338 (14)
N2'	0.5234 (9)	0.1458 (2)	0.4150 (9)	0.0385 (16)
N3'	0.0878 (8)	0.1523 (2)	0.4679 (9)	0.0403 (16)
N4'	0.2684 (8)	0.09573 (19)	0.4190 (8)	0.0414 (15)
N5'	0.0522 (9)	0.07287 (19)	0.5389 (9)	0.0573 (19)
H5'C	0.0824	0.0432	0.5453	0.069*
H5'D	−0.0338	0.0822	0.5737	0.069*
C1'	0.6654 (12)	0.1574 (3)	0.5970 (12)	0.042 (2)
C2'	0.5977 (11)	0.1822 (3)	0.7182 (12)	0.0401 (19)
C3'	0.7063 (11)	0.2010 (3)	0.9035 (11)	0.047 (2)
H3'	0.8431	0.1978	0.9848	0.056*
C4'	0.5756 (12)	0.2260 (2)	0.9497 (11)	0.044 (2)
C5'	0.3900 (11)	0.2225 (2)	0.7843 (12)	0.042 (2)
C6'	0.2387 (10)	0.1801 (2)	0.4503 (10)	0.0353 (18)
H6'	0.1792	0.2073	0.3606	0.042*
C7'	0.3144 (10)	0.1422 (2)	0.3564 (9)	0.0331 (16)
C8'	0.2162 (13)	0.1447 (3)	0.1292 (10)	0.054 (2)
H8'C	0.0851	0.1302	0.0679	0.065*
H8'D	0.2044	0.1774	0.0840	0.065*
C9'	0.3583 (12)	0.1168 (3)	0.0828 (11)	0.054 (2)
H9'C	0.3204	0.0834	0.0614	0.065*
H9'D	0.3570	0.1292	−0.0359	0.065*
C10'	0.5621 (11)	0.1224 (3)	0.2599 (10)	0.054 (2)
H10C	0.6260	0.0917	0.3057	0.065*
H10D	0.6463	0.1424	0.2277	0.065*
C11'	0.1386 (11)	0.1045 (3)	0.4752 (10)	0.0414 (18)
O2	0.674 (3)	0.0160 (8)	0.988 (4)	0.106 (9)	0.33
H2O	0.5853	−0.0018	0.9102	0.127*	0.33
C12	0.719 (13)	0.0521 (12)	0.874 (10)	0.114 (8)	0.33
H12A	0.6596	0.0820	0.8782	0.137*	0.33
H12B	0.6654	0.0419	0.7389	0.137*	0.33
H12C	0.8605	0.0559	0.9322	0.137*	0.33
O2'	0.685 (2)	0.0563 (5)	0.714 (2)	0.050 (4)	0.33
H2'O	0.6082	0.0351	0.6470	0.061*	0.33
C12'	0.694 (13)	0.0579 (13)	0.911 (6)	0.114 (8)	0.33
H12D	0.7150	0.0901	0.9586	0.137*	0.33
H12E	0.8028	0.0384	1.0030	0.137*	0.33
H12F	0.5716	0.0461	0.9003	0.137*	0.33
O2"	0.498 (4)	0.0198 (7)	0.923 (3)	0.116 (9)	0.33
H2"O	0.4092	0.0103	0.8157	0.139*	0.33
C12"	0.674 (6)	0.0334 (12)	0.902 (9)	0.114 (8)	0.33
H12G	0.6688	0.0173	0.7888	0.137*	0.33
H12H	0.7932	0.0243	1.0193	0.137*	0.33
H12I	0.6737	0.0672	0.8831	0.137*	0.33
H3N	0.731 (6)	0.4071 (16)	0.741 (6)	0.011 (14)*
H3N'	0.017 (7)	0.1669 (16)	0.510 (8)	0.022 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0534 (5)	0.0648 (6)	0.0745 (6)	−0.0168 (6)	0.0332 (5)	−0.0067 (6)
Br2	0.0839 (7)	0.0581 (6)	0.0518 (5)	−0.0186 (6)	0.0333 (5)	0.0117 (5)
O1	0.037 (4)	0.107 (5)	0.030 (3)	−0.003 (3)	0.015 (3)	0.016 (3)
N1	0.040 (4)	0.038 (3)	0.024 (3)	0.000 (3)	0.017 (3)	0.001 (3)
N2	0.040 (4)	0.047 (4)	0.035 (4)	−0.004 (3)	0.022 (3)	0.005 (3)
N3	0.052 (4)	0.043 (4)	0.030 (3)	−0.008 (3)	0.022 (3)	0.004 (3)
N4	0.043 (4)	0.035 (4)	0.041 (3)	0.000 (3)	0.027 (3)	0.008 (3)
N5	0.083 (5)	0.041 (4)	0.062 (4)	−0.010 (4)	0.056 (4)	−0.003 (3)
C1	0.043 (6)	0.052 (5)	0.027 (4)	0.004 (4)	0.020 (4)	0.001 (4)
C2	0.040 (5)	0.058 (5)	0.033 (5)	−0.001 (4)	0.022 (4)	0.006 (4)
C3	0.034 (5)	0.072 (6)	0.043 (5)	0.004 (4)	0.019 (5)	0.008 (4)
C4	0.048 (6)	0.047 (5)	0.053 (5)	−0.012 (4)	0.034 (5)	−0.005 (4)
C5	0.042 (5)	0.033 (4)	0.041 (5)	0.003 (4)	0.023 (5)	0.002 (4)
C6	0.034 (4)	0.037 (4)	0.028 (4)	0.004 (4)	0.011 (4)	0.006 (3)
C7	0.037 (4)	0.039 (5)	0.041 (4)	−0.001 (4)	0.023 (4)	0.010 (4)
C8	0.052 (6)	0.052 (6)	0.050 (6)	−0.005 (4)	0.019 (5)	−0.001 (4)
C9	0.048 (6)	0.077 (6)	0.056 (5)	0.002 (5)	0.036 (5)	0.007 (5)
C10	0.034 (5)	0.064 (6)	0.049 (5)	−0.011 (4)	0.018 (4)	0.007 (4)
C11	0.032 (5)	0.041 (5)	0.030 (4)	−0.009 (4)	0.013 (4)	0.000 (3)
Br1'	0.0479 (5)	0.0509 (5)	0.0729 (5)	0.0060 (5)	0.0341 (5)	−0.0102 (5)
Br2'	0.0692 (7)	0.0747 (7)	0.0573 (5)	0.0033 (6)	0.0247 (5)	−0.0232 (6)
O1'	0.025 (3)	0.106 (5)	0.054 (4)	0.009 (3)	0.022 (3)	−0.011 (3)
N1'	0.026 (4)	0.034 (3)	0.048 (4)	0.001 (3)	0.023 (3)	0.002 (3)
N2'	0.030 (4)	0.058 (4)	0.041 (4)	0.000 (3)	0.028 (4)	−0.001 (3)
N3'	0.027 (4)	0.051 (4)	0.057 (4)	0.000 (3)	0.030 (3)	−0.011 (3)
N4'	0.038 (4)	0.041 (4)	0.059 (4)	0.000 (3)	0.035 (3)	−0.006 (3)
N5'	0.066 (5)	0.031 (4)	0.103 (6)	−0.001 (3)	0.064 (5)	−0.008 (4)
C1'	0.037 (6)	0.052 (5)	0.047 (6)	0.005 (4)	0.029 (5)	0.007 (4)
C2'	0.036 (5)	0.046 (5)	0.050 (5)	−0.009 (4)	0.029 (5)	−0.006 (4)
C3'	0.028 (5)	0.065 (6)	0.042 (5)	0.001 (4)	0.012 (4)	0.002 (4)
C4'	0.047 (6)	0.048 (5)	0.051 (5)	0.001 (4)	0.035 (5)	0.003 (4)
C5'	0.051 (6)	0.029 (4)	0.061 (6)	0.008 (4)	0.038 (5)	−0.007 (4)
C6'	0.030 (4)	0.041 (5)	0.030 (4)	0.000 (4)	0.010 (4)	0.006 (3)
C7'	0.035 (4)	0.043 (5)	0.024 (4)	0.005 (4)	0.016 (3)	0.000 (3)
C8'	0.071 (7)	0.049 (6)	0.049 (5)	0.002 (5)	0.033 (5)	−0.004 (4)
C9'	0.068 (7)	0.059 (5)	0.053 (5)	−0.002 (5)	0.044 (5)	−0.013 (4)
C10'	0.044 (5)	0.084 (6)	0.040 (5)	0.011 (5)	0.024 (4)	0.001 (4)
C11'	0.041 (5)	0.039 (5)	0.046 (5)	−0.002 (4)	0.022 (4)	−0.006 (4)
O2	0.056 (14)	0.040 (13)	0.19 (2)	0.015 (11)	0.030 (16)	0.025 (14)
C12	0.18 (2)	0.006 (13)	0.19 (2)	0.010 (15)	0.108 (15)	−0.010 (14)
O2'	0.062 (11)	0.028 (9)	0.052 (10)	0.000 (7)	0.019 (9)	0.014 (8)
C12'	0.18 (2)	0.006 (13)	0.19 (2)	0.010 (15)	0.108 (15)	−0.010 (14)
O2"	0.21 (3)	0.050 (13)	0.084 (16)	0.001 (18)	0.07 (2)	−0.028 (11)
C12"	0.18 (2)	0.006 (13)	0.19 (2)	0.010 (15)	0.108 (15)	−0.010 (14)

Geometric parameters (Å, º) top

Br1—C4	1.878 (7)	N2'—C10'	1.506 (8)
Br2—C5	1.873 (7)	N3'—C11'	1.391 (8)
O1—C1	1.252 (7)	N3'—C6'	1.451 (8)
N1—C2	1.380 (8)	N3'—H3N'	0.855 (10)
N1—C5	1.390 (8)	N4'—C11'	1.281 (8)
N1—C6	1.480 (8)	N4'—C7'	1.489 (8)
N2—C1	1.346 (8)	N5'—C11'	1.332 (8)
N2—C7	1.436 (8)	N5'—H5'C	0.860
N2—C10	1.486 (8)	N5'—H5'D	0.860
N3—C11	1.363 (8)	C1'—C2'	1.440 (10)
N3—C6	1.411 (8)	C2'—C3'	1.362 (9)
N3—H3N	0.856 (10)	C3'—C4'	1.400 (9)
N4—C11	1.288 (7)	C3'—H3'	0.930
N4—C7	1.465 (8)	C4'—C5'	1.380 (10)
N5—C11	1.332 (8)	C6'—C7'	1.543 (8)
N5—H5AN	0.860	C6'—H6'	0.980
N5—H5BN	0.860	C7'—C8'	1.533 (9)
C1—C2	1.449 (10)	C8'—C9'	1.513 (10)
C2—C3	1.335 (10)	C8'—H8'C	0.970
C3—C4	1.390 (9)	C8'—H8'D	0.970
C3—H3	0.930	C9'—C10'	1.506 (10)
C4—C5	1.324 (9)	C9'—H9'C	0.970
C6—C7	1.517 (8)	C9'—H9'D	0.970
C6—H6	0.980	C10'—H10C	0.970
C7—C8	1.515 (9)	C10'—H10D	0.970
C8—C9	1.551 (10)	O2—C12	1.480 (4)
C8—H8A	0.970	O2—H2O	0.820
C8—H8B	0.970	C12—H12A	0.960
C9—C10	1.491 (9)	C12—H12B	0.960
C9—H9A	0.970	C12—H12C	0.960
C9—H9B	0.970	O2'—C12'	1.480 (4)
C10—H10A	0.970	O2'—H2'O	0.820
C10—H10B	0.970	C12'—H12D	0.960
Br1'—C5'	1.885 (7)	C12'—H12E	0.960
Br2'—C4'	1.840 (7)	C12'—H12F	0.960
O1'—C1'	1.220 (8)	O2"—C12"	1.480 (4)
N1'—C5'	1.346 (8)	O2"—H2"O	0.820
N1'—C2'	1.402 (8)	C12"—H12G	0.960
N1'—C6'	1.459 (8)	C12"—H12H	0.960
N2'—C1'	1.335 (9)	C12"—H12I	0.960
N2'—C7'	1.441 (8)

C2—N1—C5	106.5 (6)	C11'—N5'—H5'D	120.0
C2—N1—C6	124.8 (6)	H5'C—N5'—H5'D	120.0
C5—N1—C6	127.9 (5)	O1'—C1'—N2'	121.5 (7)
C1—N2—C7	122.2 (6)	O1'—C1'—C2'	122.9 (8)
C1—N2—C10	123.5 (6)	N2'—C1'—C2'	115.4 (7)
C7—N2—C10	112.7 (6)	C3'—C2'—N1'	108.9 (7)
C11—N3—C6	106.9 (5)	C3'—C2'—C1'	129.2 (7)
C11—N3—H3N	120 (3)	N1'—C2'—C1'	121.5 (7)
C6—N3—H3N	126 (3)	C2'—C3'—C4'	107.9 (7)
C11—N4—C7	105.5 (5)	C2'—C3'—H3'	126.1
C11—N5—H5AN	120.0	C4'—C3'—H3'	126.1
C11—N5—H5BN	120.0	C5'—C4'—C3'	106.0 (6)
H5AN—N5—H5BN	120.0	C5'—C4'—Br2'	126.3 (5)
O1—C1—N2	121.9 (7)	C3'—C4'—Br2'	127.7 (6)
O1—C1—C2	120.4 (7)	N1'—C5'—C4'	111.0 (6)
N2—C1—C2	117.5 (6)	N1'—C5'—Br1'	121.0 (6)
C3—C2—N1	108.8 (7)	C4'—C5'—Br1'	128.0 (5)
C3—C2—C1	131.8 (7)	N3'—C6'—N1'	112.3 (5)
N1—C2—C1	118.9 (7)	N3'—C6'—C7'	99.6 (5)
C2—C3—C4	107.6 (7)	N1'—C6'—C7'	111.1 (5)
C2—C3—H3	126.2	N3'—C6'—H6'	111.1
C4—C3—H3	126.2	N1'—C6'—H6'	111.1
C5—C4—C3	108.8 (7)	C7'—C6'—H6'	111.1
C5—C4—Br1	123.1 (6)	N2'—C7'—N4'	111.0 (5)
C3—C4—Br1	128.0 (6)	N2'—C7'—C8'	102.5 (6)
C4—C5—N1	108.3 (6)	N4'—C7'—C8'	110.1 (6)
C4—C5—Br2	131.7 (6)	N2'—C7'—C6'	114.5 (6)
N1—C5—Br2	119.5 (6)	N4'—C7'—C6'	104.7 (5)
N3—C6—N1	112.9 (5)	C8'—C7'—C6'	114.2 (6)
N3—C6—C7	101.5 (5)	C9'—C8'—C7'	103.2 (6)
N1—C6—C7	110.4 (5)	C9'—C8'—H8'C	111.1
N3—C6—H6	110.6	C7'—C8'—H8'C	111.1
N1—C6—H6	110.6	C9'—C8'—H8'D	111.1
C7—C6—H6	110.6	C7'—C8'—H8'D	111.1
N2—C7—N4	110.4 (5)	H8'C—C8'—H8'D	109.1
N2—C7—C8	100.4 (6)	C10'—C9'—C8'	106.4 (6)
N4—C7—C8	110.4 (6)	C10'—C9'—H9'C	110.5
N2—C7—C6	116.4 (6)	C8'—C9'—H9'C	110.5
N4—C7—C6	104.4 (5)	C10'—C9'—H9'D	110.5
C8—C7—C6	114.9 (6)	C8'—C9'—H9'D	110.5
C7—C8—C9	103.9 (6)	H9'C—C9'—H9'D	108.6
C7—C8—H8A	111.0	N2'—C10'—C9'	104.4 (6)
C9—C8—H8A	111.0	N2'—C10'—H10C	110.9
C7—C8—H8B	111.0	C9'—C10'—H10C	110.9
C9—C8—H8B	111.0	N2'—C10'—H10D	110.9
H8A—C8—H8B	109.0	C9'—C10'—H10D	110.9
C10—C9—C8	105.4 (6)	H10C—C10'—H10D	108.9
C10—C9—H9A	110.7	N4'—C11'—N5'	126.6 (7)
C8—C9—H9A	110.7	N4'—C11'—N3'	114.7 (6)
C10—C9—H9B	110.7	N5'—C11'—N3'	118.6 (6)
C8—C9—H9B	110.7	C12—O2—H2O	109.5
H9A—C9—H9B	108.8	O2—C12—H12A	109.5
N2—C10—C9	103.6 (6)	O2—C12—H12B	109.5
N2—C10—H10A	111.0	H12A—C12—H12B	109.5
C9—C10—H10A	111.0	O2—C12—H12C	109.5
N2—C10—H10B	111.0	H12A—C12—H12C	109.5
C9—C10—H10B	111.0	H12B—C12—H12C	109.5
H10A—C10—H10B	109.0	C12'—O2'—H2'O	109.5
N4—C11—N5	124.5 (6)	O2'—C12'—H12D	109.5
N4—C11—N3	115.2 (6)	O2'—C12'—H12E	109.5
N5—C11—N3	120.3 (6)	H12D—C12'—H12E	109.5
C5'—N1'—C2'	106.3 (6)	O2'—C12'—H12F	109.5
C5'—N1'—C6'	130.2 (6)	H12D—C12'—H12F	109.5
C2'—N1'—C6'	123.5 (6)	H12E—C12'—H12F	109.5
C1'—N2'—C7'	124.6 (6)	C12"—O2"—H2"O	109.5
C1'—N2'—C10'	124.3 (6)	O2"—C12"—H12G	109.5
C7'—N2'—C10'	109.4 (6)	O2"—C12"—H12H	109.5
C11'—N3'—C6'	107.6 (5)	H12G—C12"—H12H	109.5
C11'—N3'—H3N'	131 (4)	O2"—C12"—H12I	109.5
C6'—N3'—H3N'	117 (4)	H12G—C12"—H12I	109.5
C11'—N4'—C7'	106.3 (6)	H12H—C12"—H12I	109.5
C11'—N5'—H5'C	120.0

C7—N2—C1—O1	166.6 (7)	C7'—N2'—C1'—O1'	164.6 (7)
C10—N2—C1—O1	1.9 (12)	C10'—N2'—C1'—O1'	1.4 (12)
C7—N2—C1—C2	−19.0 (11)	C7'—N2'—C1'—C2'	−20.5 (10)
C10—N2—C1—C2	176.3 (7)	C10'—N2'—C1'—C2'	176.2 (7)
C5—N1—C2—C3	0.1 (8)	C5'—N1'—C2'—C3'	0.3 (7)
C6—N1—C2—C3	−170.8 (6)	C6'—N1'—C2'—C3'	−177.6 (6)
C5—N1—C2—C1	−173.0 (6)	C5'—N1'—C2'—C1'	−173.0 (6)
C6—N1—C2—C1	16.1 (10)	C6'—N1'—C2'—C1'	9.1 (9)
O1—C1—C2—C3	−4.5 (14)	O1'—C1'—C2'—C3'	−1.0 (13)
N2—C1—C2—C3	−179.0 (8)	N2'—C1'—C2'—C3'	−175.8 (7)
O1—C1—C2—N1	166.7 (7)	O1'—C1'—C2'—N1'	170.8 (7)
N2—C1—C2—N1	−7.7 (10)	N2'—C1'—C2'—N1'	−4.0 (10)
N1—C2—C3—C4	−0.7 (9)	N1'—C2'—C3'—C4'	1.0 (8)
C1—C2—C3—C4	171.2 (8)	C1'—C2'—C3'—C4'	173.6 (7)
C2—C3—C4—C5	1.0 (9)	C2'—C3'—C4'—C5'	−1.9 (8)
C2—C3—C4—Br1	−180.0 (6)	C2'—C3'—C4'—Br2'	179.1 (5)
C3—C4—C5—N1	−1.0 (8)	C2'—N1'—C5'—C4'	−1.5 (7)
Br1—C4—C5—N1	179.9 (4)	C6'—N1'—C5'—C4'	176.2 (6)
C3—C4—C5—Br2	−172.8 (6)	C2'—N1'—C5'—Br1'	177.5 (5)
Br1—C4—C5—Br2	8.2 (10)	C6'—N1'—C5'—Br1'	−4.7 (9)
C2—N1—C5—C4	0.6 (8)	C3'—C4'—C5'—N1'	2.1 (8)
C6—N1—C5—C4	171.0 (6)	Br2'—C4'—C5'—N1'	−178.8 (5)
C2—N1—C5—Br2	173.5 (5)	C3'—C4'—C5'—Br1'	−176.8 (5)
C6—N1—C5—Br2	−16.0 (9)	Br2'—C4'—C5'—Br1'	2.3 (10)
C11—N3—C6—N1	−94.3 (6)	C11'—N3'—C6'—N1'	−93.3 (7)
C11—N3—C6—C7	23.9 (7)	C11'—N3'—C6'—C7'	24.4 (7)
C2—N1—C6—N3	114.2 (7)	C5'—N1'—C6'—N3'	−59.1 (9)
C5—N1—C6—N3	−54.7 (8)	C2'—N1'—C6'—N3'	118.4 (6)
C2—N1—C6—C7	1.3 (8)	C5'—N1'—C6'—C7'	−169.6 (6)
C5—N1—C6—C7	−167.5 (6)	C2'—N1'—C6'—C7'	7.8 (8)
C1—N2—C7—N4	−81.8 (8)	C1'—N2'—C7'—N4'	−80.5 (8)
C10—N2—C7—N4	84.4 (7)	C10'—N2'—C7'—N4'	84.9 (6)
C1—N2—C7—C8	161.7 (7)	C1'—N2'—C7'—C8'	162.0 (7)
C10—N2—C7—C8	−32.1 (8)	C10'—N2'—C7'—C8'	−32.7 (8)
C1—N2—C7—C6	37.0 (10)	C1'—N2'—C7'—C6'	37.7 (10)
C10—N2—C7—C6	−156.8 (6)	C10'—N2'—C7'—C6'	−156.9 (6)
C11—N4—C7—N2	141.5 (6)	C11'—N4'—C7'—N2'	141.7 (6)
C11—N4—C7—C8	−108.4 (6)	C11'—N4'—C7'—C8'	−105.5 (7)
C11—N4—C7—C6	15.6 (7)	C11'—N4'—C7'—C6'	17.7 (7)
N3—C6—C7—N2	−146.0 (6)	N3'—C6'—C7'—N2'	−146.8 (6)
N1—C6—C7—N2	−26.0 (8)	N1'—C6'—C7'—N2'	−28.3 (8)
N3—C6—C7—N4	−24.0 (6)	N3'—C6'—C7'—N4'	−25.1 (6)
N1—C6—C7—N4	96.0 (6)	N1'—C6'—C7'—N4'	93.4 (6)
N3—C6—C7—C8	97.0 (7)	N3'—C6'—C7'—C8'	95.4 (7)
N1—C6—C7—C8	−143.0 (6)	N1'—C6'—C7'—C8'	−146.1 (6)
N2—C7—C8—C9	36.8 (8)	N2'—C7'—C8'—C9'	37.5 (8)
N4—C7—C8—C9	−79.8 (7)	N4'—C7'—C8'—C9'	−80.6 (7)
C6—C7—C8—C9	162.6 (6)	C6'—C7'—C8'—C9'	161.9 (6)
C7—C8—C9—C10	−30.3 (8)	C7'—C8'—C9'—C10'	−29.2 (8)
C1—N2—C10—C9	179.5 (7)	C1'—N2'—C10'—C9'	−179.8 (7)
C7—N2—C10—C9	13.5 (8)	C7'—N2'—C10'—C9'	14.7 (8)
C8—C9—C10—N2	11.0 (7)	C8'—C9'—C10'—N2'	9.9 (8)
C7—N4—C11—N5	178.4 (6)	C7'—N4'—C11'—N5'	178.4 (7)
C7—N4—C11—N3	−0.5 (8)	C7'—N4'—C11'—N3'	−2.1 (8)
C6—N3—C11—N4	−16.2 (8)	C6'—N3'—C11'—N4'	−15.7 (8)
C6—N3—C11—N5	164.9 (6)	C6'—N3'—C11'—N5'	163.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.86 (1)	2.14 (3)	2.921 (7)	151 (4)
N5—H5BN···O1ⁱ	0.86	2.36	3.096 (7)	143
N5—H5AN···N4′ⁱⁱ	0.86	2.13	2.981 (8)	171
N3′—H3N′···O1′ⁱⁱⁱ	0.86 (1)	2.13 (3)	2.833 (7)	139 (5)
N5′—H5′D···O1′ⁱⁱⁱ	0.86	2.34	3.062 (7)	142
N5′—H5′C···N4^iv	0.86	2.12	2.961 (7)	167

Symmetry codes: (i) x, y, z+1; (ii) −x+1, y+1/2, −z+1; (iii) x−1, y, z; (iv) −x+1, y−1/2, −z+1.

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Di­bromo­phakellin methanol hemisolvate

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Dibromophakellin methanol hemisolvate