#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:02:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178970 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/99/4119903.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_4119903
loop_
_publ_author_name
'Holger Braunschweig'
'Alexander Damme'
'Rian D. Dewhurst'
'Thomas Kramer'
'Thomas Kupfer'
'Krzysztof Radacki'
'Eva Siedler'
'Alexandra Trumpp'
'Katharina Wagner'
'Christine Werner'
_publ_contact_author_address
; Institut für Anorganische Chemie
Universität Würzburg
Am Hubland
97074 Würzburg, Germany
;
_publ_contact_author_email       H.Braunschweig@mail.uni-wuerzburg.de
_publ_contact_author_fax         +49-931-3184623
_publ_contact_author_name        'Prof. Dr. Holger Braunschweig'
_publ_contact_author_phone       +49-931-3185260
_publ_section_title
;
 Quaternizing Diboranes(4): Highly Divergent Outcomes and an Inorganic
 Wagner-Meerwein Rearrangement
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8702
_journal_page_last               8707
_journal_paper_doi               10.1021/ja403037k
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C15 H28 B Cl N2'
_chemical_formula_sum            'C15 H28 B Cl N2'
_chemical_formula_weight         282.65
_chemical_name_common
;
?
;
_chemical_name_systematic
; 
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.7756(6)
_cell_length_b                   12.1660(7)
_cell_length_c                   25.4888(16)
_cell_measurement_reflns_used    5167
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.48
_cell_volume                     3341.5(3)
_computing_cell_refinement       'Saint+ ver. 7.68A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2010.3 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68A (Bruker AXS)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21353
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.75
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs 2008/1 (Bruker 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0426P)²+1.9084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                2777
_reflns_number_total             3496
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja403037k_si_001_09.cif
_cod_data_source_block           18d
_cod_database_code               4119903
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.07795(4) 0.97547(4) 0.170914(16) 0.02211(12) Uani 1 1 d U
B1 B -0.07533(17) 0.89339(17) 0.15491(7) 0.0193(4) Uani 1 1 d U
C1_1 C -0.02805(14) 0.76383(14) 0.15455(6) 0.0163(3) Uani 1 1 d U
N2_1 N 0.03965(13) 0.68536(12) 0.12889(5) 0.0184(3) Uani 1 1 d U
C3_1 C 0.04621(15) 0.59199(15) 0.15978(7) 0.0208(4) Uani 1 1 d U
H3_1 H 0.0870 0.5254 0.1508 0.025 Uiso 1 1 calc R
C4_1 C -0.01517(15) 0.61182(14) 0.20476(6) 0.0185(4) Uani 1 1 d U
H4_1 H -0.0257 0.5629 0.2335 0.022 Uiso 1 1 calc R
N5_1 N -0.05939(11) 0.71693(11) 0.20058(5) 0.0157(3) Uani 1 1 d U
C1_2 C 0.09933(17) 0.69255(16) 0.07544(6) 0.0243(4) Uani 1 1 d U
C2_2 C 0.17685(18) 0.79677(17) 0.07270(7) 0.0315(5) Uani 1 1 d U
H2A_2 H 0.1244 0.8605 0.0806 0.047 Uiso 1 1 calc R
H2B_2 H 0.2118 0.8045 0.0374 0.047 Uiso 1 1 calc R
H2C_2 H 0.2444 0.7925 0.0984 0.047 Uiso 1 1 calc R
C3_2 C -0.00285(18) 0.68828(17) 0.03387(7) 0.0309(4) Uani 1 1 d U
H3A_2 H -0.0461 0.6176 0.0360 0.046 Uiso 1 1 calc R
H3B_2 H 0.0341 0.6964 -0.0010 0.046 Uiso 1 1 calc R
H3C_2 H -0.0620 0.7481 0.0400 0.046 Uiso 1 1 calc R
C4_2 C 0.1856(2) 0.59376(18) 0.06748(8) 0.0377(5) Uani 1 1 d U
H4A_2 H 0.2460 0.5907 0.0962 0.057 Uiso 1 1 calc R
H4B_2 H 0.2295 0.6014 0.0340 0.057 Uiso 1 1 calc R
H4C_2 H 0.1365 0.5260 0.0671 0.057 Uiso 1 1 calc R
C2_3 C -0.16010(15) 0.88670(14) 0.20862(6) 0.0198(4) Uani 1 1 d U
H2A_3 H -0.1459 0.9532 0.2302 0.024 Uiso 1 1 calc R
H2B_3 H -0.2491 0.8842 0.1991 0.024 Uiso 1 1 calc R
C1_3 C -0.12621(14) 0.78405(14) 0.24045(6) 0.0167(3) Uani 1 1 d U
C3_3 C -0.03785(16) 0.80789(15) 0.28586(6) 0.0220(4) Uani 1 1 d U
H3A_3 H -0.0103 0.7385 0.3015 0.033 Uiso 1 1 calc R
H3B_3 H -0.0808 0.8519 0.3124 0.033 Uiso 1 1 calc R
H3C_3 H 0.0343 0.8486 0.2728 0.033 Uiso 1 1 calc R
C4_3 C -0.23750(15) 0.71909(14) 0.26043(7) 0.0218(4) Uani 1 1 d U
H4A_3 H -0.2892 0.6966 0.2307 0.033 Uiso 1 1 calc R
H4B_3 H -0.2864 0.7652 0.2842 0.033 Uiso 1 1 calc R
H4C_3 H -0.2085 0.6537 0.2792 0.033 Uiso 1 1 calc R
C1_4 C -0.14937(15) 0.95541(14) 0.10707(6) 0.0197(4) Uani 1 1 d U
C2_4 C -0.26235(16) 0.88673(16) 0.08983(7) 0.0252(4) Uani 1 1 d U
H2A_4 H -0.3095 0.9274 0.0633 0.038 Uiso 1 1 calc R
H2B_4 H -0.3155 0.8723 0.1203 0.038 Uiso 1 1 calc R
H2C_4 H -0.2339 0.8169 0.0750 0.038 Uiso 1 1 calc R
C3_4 C -0.07424(18) 0.98619(16) 0.05822(7) 0.0281(4) Uani 1 1 d U
H3A_4 H -0.0480 0.9191 0.0400 0.042 Uiso 1 1 calc R
H3B_4 H -0.0009 1.0285 0.0687 0.042 Uiso 1 1 calc R
H3C_4 H -0.1257 1.0306 0.0347 0.042 Uiso 1 1 calc R
C4_4 C -0.19928(17) 1.06529(15) 0.12911(7) 0.0268(4) Uani 1 1 d U
H4A_4 H -0.1296 1.1106 0.1411 0.040 Uiso 1 1 calc R
H4B_4 H -0.2551 1.0505 0.1586 0.040 Uiso 1 1 calc R
H4C_4 H -0.2447 1.1045 0.1015 0.040 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1_4 B1 C2_3 111.75(14)
C1_4 B1 C1_1 125.66(14)
C2_3 B1 C1_1 97.36(13)
C1_4 B1 Cl1 109.15(12)
C2_3 B1 Cl1 108.50(12)
C1_1 B1 Cl1 103.02(11)
N5_1 C1_1 N2_1 104.74(14)
N5_1 C1_1 B1 108.73(14)
N2_1 C1_1 B1 146.17(15)
C1_1 N2_1 C3_1 109.15(13)
C1_1 N2_1 C1_2 128.20(14)
C3_1 N2_1 C1_2 122.64(14)
C4_1 C3_1 N2_1 108.21(15)
C4_1 C3_1 H3_1 125.9
N2_1 C3_1 H3_1 125.9
C3_1 C4_1 N5_1 105.81(15)
C3_1 C4_1 H4_1 127.1
N5_1 C4_1 H4_1 127.1
C1_1 N5_1 C4_1 112.09(14)
C1_1 N5_1 C1_3 118.88(13)
C4_1 N5_1 C1_3 128.87(13)
N2_1 C1_2 C2_2 108.91(14)
N2_1 C1_2 C3_2 108.47(14)
C2_2 C1_2 C3_2 113.09(16)
N2_1 C1_2 C4_2 109.42(14)
C2_2 C1_2 C4_2 108.34(16)
C3_2 C1_2 C4_2 108.56(15)
C1_2 C2_2 H2A_2 109.5
C1_2 C2_2 H2B_2 109.5
H2A_2 C2_2 H2B_2 109.5
C1_2 C2_2 H2C_2 109.5
H2A_2 C2_2 H2C_2 109.5
H2B_2 C2_2 H2C_2 109.5
C1_2 C3_2 H3A_2 109.5
C1_2 C3_2 H3B_2 109.5
H3A_2 C3_2 H3B_2 109.5
C1_2 C3_2 H3C_2 109.5
H3A_2 C3_2 H3C_2 109.5
H3B_2 C3_2 H3C_2 109.5
C1_2 C4_2 H4A_2 109.5
C1_2 C4_2 H4B_2 109.5
H4A_2 C4_2 H4B_2 109.5
C1_2 C4_2 H4C_2 109.5
H4A_2 C4_2 H4C_2 109.5
H4B_2 C4_2 H4C_2 109.5
C1_3 C2_3 B1 110.35(13)
C1_3 C2_3 H2A_3 109.6
B1 C2_3 H2A_3 109.6
C1_3 C2_3 H2B_3 109.6
B1 C2_3 H2B_3 109.6
H2A_3 C2_3 H2B_3 108.1
N5_1 C1_3 C4_3 108.92(13)
N5_1 C1_3 C3_3 108.66(13)
C4_3 C1_3 C3_3 109.63(13)
N5_1 C1_3 C2_3 101.58(12)
C4_3 C1_3 C2_3 114.32(13)
C3_3 C1_3 C2_3 113.26(14)
C1_3 C3_3 H3A_3 109.5
C1_3 C3_3 H3B_3 109.5
H3A_3 C3_3 H3B_3 109.5
C1_3 C3_3 H3C_3 109.5
H3A_3 C3_3 H3C_3 109.5
H3B_3 C3_3 H3C_3 109.5
C1_3 C4_3 H4A_3 109.5
C1_3 C4_3 H4B_3 109.5
H4A_3 C4_3 H4B_3 109.5
C1_3 C4_3 H4C_3 109.5
H4A_3 C4_3 H4C_3 109.5
H4B_3 C4_3 H4C_3 109.5
C3_4 C1_4 C2_4 108.56(14)
C3_4 C1_4 C4_4 105.53(14)
C2_4 C1_4 C4_4 107.32(14)
C3_4 C1_4 B1 117.35(14)
C2_4 C1_4 B1 110.30(14)
C4_4 C1_4 B1 107.25(14)
C1_4 C2_4 H2A_4 109.5
C1_4 C2_4 H2B_4 109.5
H2A_4 C2_4 H2B_4 109.5
C1_4 C2_4 H2C_4 109.5
H2A_4 C2_4 H2C_4 109.5
H2B_4 C2_4 H2C_4 109.5
C1_4 C3_4 H3A_4 109.5
C1_4 C3_4 H3B_4 109.5
H3A_4 C3_4 H3B_4 109.5
C1_4 C3_4 H3C_4 109.5
H3A_4 C3_4 H3C_4 109.5
H3B_4 C3_4 H3C_4 109.5
C1_4 C4_4 H4A_4 109.5
C1_4 C4_4 H4B_4 109.5
H4A_4 C4_4 H4B_4 109.5
C1_4 C4_4 H4C_4 109.5
H4A_4 C4_4 H4C_4 109.5
H4B_4 C4_4 H4C_4 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 B1 1.9728(19)
B1 C1_4 1.641(2)
B1 C2_3 1.648(2)
B1 C1_1 1.657(3)
C1_1 N5_1 1.348(2)
C1_1 N2_1 1.368(2)
N2_1 C3_1 1.384(2)
N2_1 C1_2 1.509(2)
C3_1 C4_1 1.345(2)
C3_1 H3_1 0.9500
C4_1 N5_1 1.369(2)
C4_1 H4_1 0.9500
N5_1 C1_3 1.489(2)
C1_2 C2_2 1.520(3)
C1_2 C3_2 1.529(2)
C1_2 C4_2 1.533(3)
C2_2 H2A_2 0.9800
C2_2 H2B_2 0.9800
C2_2 H2C_2 0.9800
C3_2 H3A_2 0.9800
C3_2 H3B_2 0.9800
C3_2 H3C_2 0.9800
C4_2 H4A_2 0.9800
C4_2 H4B_2 0.9800
C4_2 H4C_2 0.9800
C2_3 C1_3 1.533(2)
C2_3 H2A_3 0.9900
C2_3 H2B_3 0.9900
C1_3 C4_3 1.524(2)
C1_3 C3_3 1.527(2)
C3_3 H3A_3 0.9800
C3_3 H3B_3 0.9800
C3_3 H3C_3 0.9800
C4_3 H4A_3 0.9800
C4_3 H4B_3 0.9800
C4_3 H4C_3 0.9800
C1_4 C3_4 1.532(2)
C1_4 C2_4 1.541(2)
C1_4 C4_4 1.547(2)
C2_4 H2A_4 0.9800
C2_4 H2B_4 0.9800
C2_4 H2C_4 0.9800
C3_4 H3A_4 0.9800
C3_4 H3B_4 0.9800
C3_4 H3C_4 0.9800
C4_4 H4A_4 0.9800
C4_4 H4B_4 0.9800
C4_4 H4C_4 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1_4 B1 C1_1 N5_1 -133.80(16)
C2_3 B1 C1_1 N5_1 -10.26(16)
Cl1 B1 C1_1 N5_1 100.73(12)
C1_4 B1 C1_1 N2_1 55.0(3)
C2_3 B1 C1_1 N2_1 178.6(2)
Cl1 B1 C1_1 N2_1 -70.5(3)
N5_1 C1_1 N2_1 C3_1 0.84(17)
B1 C1_1 N2_1 C3_1 172.2(2)
N5_1 C1_1 N2_1 C1_2 -179.74(14)
B1 C1_1 N2_1 C1_2 -8.4(3)
C1_1 N2_1 C3_1 C4_1 -0.84(19)
C1_2 N2_1 C3_1 C4_1 179.69(14)
N2_1 C3_1 C4_1 N5_1 0.48(18)
N2_1 C1_1 N5_1 C4_1 -0.55(17)
B1 C1_1 N5_1 C4_1 -175.49(13)
N2_1 C1_1 N5_1 C1_3 175.22(13)
B1 C1_1 N5_1 C1_3 0.28(18)
C3_1 C4_1 N5_1 C1_1 0.05(18)
C3_1 C4_1 N5_1 C1_3 -175.19(14)
C1_1 N2_1 C1_2 C2_2 51.0(2)
C3_1 N2_1 C1_2 C2_2 -129.62(17)
C1_1 N2_1 C1_2 C3_2 -72.4(2)
C3_1 N2_1 C1_2 C3_2 106.91(18)
C1_1 N2_1 C1_2 C4_2 169.29(17)
C3_1 N2_1 C1_2 C4_2 -11.4(2)
C1_4 B1 C2_3 C1_3 150.05(14)
C1_1 B1 C2_3 C1_3 16.86(16)
Cl1 B1 C2_3 C1_3 -89.56(14)
C1_1 N5_1 C1_3 C4_3 131.72(14)
C4_1 N5_1 C1_3 C4_3 -53.3(2)
C1_1 N5_1 C1_3 C3_3 -108.91(15)
C4_1 N5_1 C1_3 C3_3 66.1(2)
C1_1 N5_1 C1_3 C2_3 10.74(17)
C4_1 N5_1 C1_3 C2_3 -174.29(15)
B1 C2_3 C1_3 N5_1 -17.15(16)
B1 C2_3 C1_3 C4_3 -134.27(14)
B1 C2_3 C1_3 C3_3 99.19(16)
C2_3 B1 C1_4 C3_4 169.15(15)
C1_1 B1 C1_4 C3_4 -73.7(2)
Cl1 B1 C1_4 C3_4 49.14(18)
C2_3 B1 C1_4 C2_4 -65.86(18)
C1_1 B1 C1_4 C2_4 51.3(2)
Cl1 B1 C1_4 C2_4 174.13(11)
C2_3 B1 C1_4 C4_4 50.71(18)
C1_1 B1 C1_4 C4_4 167.83(15)
Cl1 B1 C1_4 C4_4 -69.30(15)
