#------------------------------------------------------------------------------
#$Date: 2016-02-16 18:55:33 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176466 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/07/8100761.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8100761
loop_
_publ_author_name
'Euler, H.'
'Kirfel, A.'
'Freudenthal, S.J.'
'Müller, C.E.'
_publ_section_title
;
Crystal structure of 8-(5-bromopentyl)-4,4-difluoro-1,3,5,7-tetramethyl-
4-bora-3a,4a-diaza-s-indacene, C₁₈H₂₄BBrF₂N₂
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              543
_journal_page_last               545
_journal_volume                  217
_journal_year                    2002
_chemical_formula_structural     'C18 H24 B1 Br1 F2 N2'
_chemical_formula_sum            'C18 H24 B Br F2 N2'
_chemical_formula_weight         397.11
_chemical_melting_point          408.15
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                95.491(13)
_cell_angle_beta                 90.764(12)
_cell_angle_gamma                106.724(9)
_cell_formula_units_Z            4
_cell_length_a                   13.6457(16)
_cell_length_b                   13.9735(19)
_cell_length_c                   10.3344(18)
_cell_measurement_temperature    295(2)
_cell_volume                     1876.8(5)
_diffrn_ambient_temperature      295(2)
_exptl_crystal_density_diffrn    1.405
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '135\%C' was changed to '408.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_formula_sum        'C18 H24 B1 Br1 F2 N2'
_cod_database_code               8100761
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.56827(13) 0.14011(14) -0.00946(16) 0.1322(8) Uani 1 2 i d . . .
F1 F 0.1279(5) 0.4503(5) -0.6187(6) 0.082(2) Uani 1 2 i d . . .
F2 F 0.2638(5) 0.5680(5) -0.6840(6) 0.089(2) Uani 1 2 i d . . .
N3A N 0.2835(7) 0.4069(8) -0.6495(10) 0.064(3) Uani 1 2 i d . . .
N4A N 0.2689(7) 0.5232(8) -0.4667(10) 0.058(3) Uani 1 2 i d . . .
B4 B 0.2332(11) 0.4897(11) -0.6068(15) 0.057(4) Uani 1 2 i d . . .
C1 C 0.3802(10) 0.2969(11) -0.6580(17) 0.085(4) Uani 1 2 i d . . .
C2 C 0.3247(13) 0.2845(11) -0.7731(15) 0.098(5) Uani 1 2 i d . . .
H21 H 0.3234 0.2373 -0.8435 0.050 Uiso 1 2 i calc . . .
C3 C 0.2700(10) 0.3564(12) -0.7653(16) 0.080(4) Uani 1 2 i d . . .
C5 C 0.2397(10) 0.5922(12) -0.3899(17) 0.084(4) Uani 1 2 i d . . .
C6 C 0.2880(13) 0.6024(11) -0.2711(15) 0.099(5) Uani 1 2 i d . . .
H61 H 0.2772 0.6436 -0.1998 0.050 Uiso 1 2 i calc . . .
C7 C 0.3527(10) 0.5465(11) -0.2685(14) 0.080(4) Uani 1 2 i d . . .
C7A C 0.3391(8) 0.4923(9) -0.3956(13) 0.056(3) Uani 1 2 i d . . .
C8 C 0.3832(7) 0.4197(10) -0.4508(13) 0.055(3) Uani 1 2 i d . . .
C8A C 0.3554(8) 0.3745(10) -0.5771(15) 0.059(3) Uani 1 2 i d . . .
C9 C 0.4484(10) 0.2342(9) -0.6285(14) 0.107(5) Uani 1 2 i d . . .
H91 H 0.4798 0.2561 -0.5430 0.050 Uiso 1 2 i calc . . .
H92 H 0.5006 0.2413 -0.6913 0.050 Uiso 1 2 i calc . . .
H93 H 0.4086 0.1650 -0.6324 0.050 Uiso 1 2 i calc . . .
C10 C 0.2007(10) 0.3669(11) -0.8734(13) 0.115(5) Uani 1 2 i d . . .
H101 H 0.1718 0.4205 -0.8477 0.050 Uiso 1 2 i calc . . .
H102 H 0.1466 0.3052 -0.8919 0.050 Uiso 1 2 i calc . . .
H103 H 0.2392 0.3816 -0.9498 0.050 Uiso 1 2 i calc . . .
C11 C 0.1624(10) 0.6412(10) -0.4276(14) 0.111(5) Uani 1 2 i d . . .
H111 H 0.1409 0.6202 -0.5172 0.050 Uiso 1 2 i calc . . .
H112 H 0.1918 0.7129 -0.4159 0.050 Uiso 1 2 i calc . . .
H113 H 0.1044 0.6224 -0.3741 0.050 Uiso 1 2 i calc . . .
C12 C 0.4186(11) 0.5428(11) -0.1532(13) 0.124(5) Uani 1 2 i d . . .
H121 H 0.4585 0.4978 -0.1758 0.050 Uiso 1 2 i calc . . .
H122 H 0.3760 0.5195 -0.0827 0.050 Uiso 1 2 i calc . . .
H123 H 0.4635 0.6088 -0.1270 0.050 Uiso 1 2 i calc . . .
C1' C 0.4600(8) 0.3870(8) -0.3761(11) 0.071(4) Uani 1 2 i d . . .
H1'1 H 0.5037 0.4443 -0.3218 0.050 Uiso 1 2 i calc . . .
H1'2 H 0.5028 0.3615 -0.4362 0.050 Uiso 1 2 i calc . . .
C2' C 0.4066(9) 0.3045(10) -0.2897(13) 0.096(4) Uani 1 2 i d . . .
H2'1 H 0.3755 0.2423 -0.3443 0.050 Uiso 1 2 i calc . . .
H2'2 H 0.3526 0.3241 -0.2441 0.050 Uiso 1 2 i calc . . .
C3' C 0.4839(11) 0.2869(11) -0.1889(13) 0.106(5) Uani 1 2 i d . . .
H3'1 H 0.5261 0.3514 -0.1487 0.050 Uiso 1 2 i calc . . .
H3'2 H 0.4461 0.2507 -0.1211 0.050 Uiso 1 2 i calc . . .
C4' C 0.5489(11) 0.2314(10) -0.2460(14) 0.098(5) Uani 1 2 i d . . .
H4'1 H 0.5846 0.2660 -0.3164 0.050 Uiso 1 2 i calc . . .
H4'2 H 0.5070 0.1656 -0.2827 0.050 Uiso 1 2 i calc . . .
C5' C 0.6276(9) 0.2185(9) -0.1476(13) 0.094(4) Uani 1 2 i d . . .
H5'1 H 0.6683 0.2845 -0.1098 0.050 Uiso 1 2 i calc . . .
H5'2 H 0.6734 0.1865 -0.1932 0.050 Uiso 1 2 i calc . . .
Br* Br 1.09901(12) -0.35494(14) -1.01615(15) 0.1284(8) Uani 1 2 i d . . .
F1* F 0.8022(4) 0.1377(5) -0.3751(6) 0.0731(18) Uani 1 2 i d . . .
F2* F 0.6632(4) 0.0092(4) -0.3436(5) 0.0773(19) Uani 1 2 i d . . .
N3A* N 0.7522(6) -0.0009(6) -0.5410(9) 0.053(2) Uani 1 2 i d . . .
N4A* N 0.8284(6) -0.0191(6) -0.3305(10) 0.051(2) Uani 1 2 i d . . .
B4* B 0.7596(10) 0.0348(13) -0.3952(14) 0.058(4) Uani 1 2 i d . . .
C1* C 0.7792(8) -0.0694(9) -0.7401(11) 0.056(3) Uani 1 2 i d . . .
C2* C 0.7103(9) -0.0172(9) -0.7524(13) 0.066(3) Uani 1 2 i d . . .
H2*1 H 0.6790 -0.0103 -0.8301 0.050 Uiso 1 2 i calc . . .
C3* C 0.6944(8) 0.0242(9) -0.6304(14) 0.063(3) Uani 1 2 i d . . .
C5* C 0.8510(9) -0.0116(8) -0.2054(13) 0.059(3) Uani 1 2 i d . . .
C6* C 0.9193(9) -0.0650(9) -0.1828(11) 0.061(3) Uani 1 2 i d . . .
H6*1 H 0.9465 -0.0701 -0.1016 0.050 Uiso 1 2 i calc . . .
C7* C 0.9405(7) -0.1089(8) -0.2981(12) 0.051(3) Uani 1 2 i d . . .
C7A* C 0.8836(8) -0.0788(8) -0.3967(12) 0.048(3) Uani 1 2 i d . . .
C8* C 0.8741(7) -0.0965(7) -0.5324(11) 0.045(3) Uani 1 2 i d . . .
C8A* C 0.8083(8) -0.0615(8) -0.6055(11) 0.052(3) Uani 1 2 i d . . .
C9* C 0.8134(8) -0.1283(9) -0.8496(11) 0.069(3) Uani 1 2 i d . . .
H9*1 H 0.8622 -0.1586 -0.8167 0.050 Uiso 1 2 i calc . . .
H9*2 H 0.8446 -0.0844 -0.9130 0.050 Uiso 1 2 i calc . . .
H9*3 H 0.7553 -0.1799 -0.8894 0.050 Uiso 1 2 i calc . . .
C10* C 0.6257(9) 0.0880(9) -0.6031(11) 0.084(4) Uani 1 2 i d . . .
H101 H 0.6284 0.1081 -0.5113 0.050 Uiso 1 2 i calc . . .
H102 H 0.5568 0.0507 -0.6312 0.050 Uiso 1 2 i calc . . .
H103 H 0.6475 0.1466 -0.6490 0.050 Uiso 1 2 i calc . . .
C11* C 0.8080(9) 0.0475(10) -0.1074(11) 0.086(4) Uani 1 2 i d . . .
H111 H 0.7626 0.0769 -0.1501 0.050 Uiso 1 2 i calc . . .
H112 H 0.8627 0.0998 -0.0620 0.050 Uiso 1 2 i calc . . .
H112 H 0.7709 0.0043 -0.0466 0.050 Uiso 1 2 i calc . . .
C12* C 1.0096(8) -0.1732(8) -0.3143(9) 0.063(3) Uani 1 2 i d . . .
H121 H 1.0113 -0.1954 -0.4049 0.050 Uiso 1 2 i calc . . .
H122 H 0.9851 -0.2304 -0.2666 0.050 Uiso 1 2 i calc . . .
H123 H 1.0774 -0.1354 -0.2820 0.050 Uiso 1 2 i calc . . .
C1'* C 0.9361(7) -0.1572(8) -0.6008(9) 0.048(3) Uani 1 2 i d . . .
H1'1 H 1.0013 -0.1436 -0.5533 0.050 Uiso 1 2 i calc . . .
H1'2 H 0.9501 -0.1358 -0.6869 0.050 Uiso 1 2 i calc . . .
C2'* C 0.8837(8) -0.2704(9) -0.6140(10) 0.059(3) Uani 1 2 i d . . .
H2'1 H 0.8241 -0.2853 -0.6729 0.050 Uiso 1 2 i calc . . .
H2'2 H 0.8601 -0.2901 -0.5297 0.050 Uiso 1 2 i calc . . .
C3'* C 0.9535(9) -0.3330(8) -0.6646(12) 0.075(4) Uani 1 2 i d . . .
H3'1 H 1.0149 -0.3149 -0.6083 0.050 Uiso 1 2 i calc . . .
H3'2 H 0.9185 -0.4034 -0.6587 0.050 Uiso 1 2 i calc . . .
C4'* C 0.9835(9) -0.3205(10) -0.7982(13) 0.087(4) Uani 1 2 i d . . .
H4'1 H 1.0114 -0.2493 -0.8066 0.050 Uiso 1 2 i calc . . .
H4'2 H 0.9229 -0.3459 -0.8557 0.050 Uiso 1 2 i calc . . .
C5'* C 1.0623(9) -0.3736(9) -0.8426(13) 0.098(4) Uani 1 2 i d . . .
H5'1 H 1.0346 -0.4449 -0.8351 0.050 Uiso 1 2 i calc . . .
H5'2 H 1.1232 -0.3483 -0.7856 0.050 Uiso 1 2 i calc . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br C5' 1.927(13) . ?
F1 B4 1.382(13) . ?
F2 B4 1.386(14) . ?
N3A C3 1.312(14) . ?
N3A C8A 1.424(12) . ?
N3A B4 1.541(15) . ?
N4A C5 1.343(15) . ?
N4A C7A 1.387(12) . ?
N4A B4 1.508(15) . ?
C1 C2 1.371(16) . ?
C1 C8A 1.427(16) . ?
C1 C9 1.497(17) . ?
C2 C3 1.411(17) . ?
C3 C10 1.499(17) . ?
C5 C6 1.361(16) . ?
C5 C11 1.479(17) . ?
C6 C7 1.339(16) . ?
C7 C7A 1.434(15) . ?
C7 C12 1.497(16) . ?
C7A C8 1.402(14) . ?
C8 C8A 1.391(15) . ?
C8 C1' 1.492(14) . ?
C1' C2' 1.545(14) . ?
C2' C3' 1.558(15) . ?
C3' C4' 1.435(17) . ?
C4' C5' 1.527(16) . ?
Br* C5'* 1.890(13) . ?
F1* B4* 1.381(15) . ?
F2* B4* 1.389(13) . ?
N3A* C3* 1.341(12) . ?
N3A* C8A* 1.423(12) . ?
N3A* B4* 1.535(15) . ?
N4A* C5* 1.312(12) . ?
N4A* C7A* 1.413(11) . ?
N4A* B4* 1.544(15) . ?
C1* C2* 1.357(13) . ?
C1* C8A* 1.427(13) . ?
C1* C9* 1.494(14) . ?
C2* C3* 1.383(14) . ?
C3* C10* 1.481(14) . ?
C5* C6* 1.381(13) . ?
C5* C11* 1.479(15) . ?
C6* C7* 1.361(13) . ?
C7* C7A* 1.437(13) . ?
C7* C12* 1.479(13) . ?
C7A* C8* 1.398(13) . ?
C8* C8A* 1.386(13) . ?
C8* C1'* 1.501(13) . ?
C1'* C2'* 1.528(13) . ?
C2'* C3'* 1.533(14) . ?
C3'* C4'* 1.458(14) . ?
C4'* C5'* 1.525(15) . ?
