#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:24:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180181 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/77/7107780.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_7107780
loop_
_publ_author_name
'Sarah Robinson'
'Jonathan McMaster'
'William Lewis'
'Alexander J. Blake'
'Stephen T. Liddle'
_publ_section_title
;
 Alkali-metal mediated reactivity of a diaminobromoborane: mono- and
 bis-borylation of naphthalene versus boryl lithium or hydroborane
 formation
;
_journal_name_full               Chem.Commun.
_journal_page_first              5769
_journal_paper_doi               10.1039/c2cc31758c
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C36 H50 B BR N2, C7 H8'
_chemical_formula_sum            'C43 H58 B Br N2'
_chemical_formula_weight         693.63
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   'geom, Me from difmap'
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 91.785(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.3321(7)
_cell_length_b                   10.0841(4)
_cell_length_c                   22.7728(10)
_cell_measurement_reflns_used    6889
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      2.34
_cell_volume                     3978.3(3)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material
'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23033
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         4440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0419
_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)+(0.0614P)²+2.0030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                3541
_reflns_number_total             4440
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc31758c.txt
_cod_data_source_block           bsrbrb
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7107780
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Br1 Br 0.0000 0.04079(3) 0.7500 0.03428(13) Uani 1 2 d S
B1 B 0.0000 0.2314(3) 0.7500 0.0196(6) Uani 1 2 d S
N1 N -0.05595(9) 0.31379(16) 0.77618(7) 0.0212(4) Uani 1 1 d .
C1 C -0.03358(11) 0.44631(18) 0.76644(9) 0.0208(4) Uani 1 1 d .
C2 C -0.06726(12) 0.56387(19) 0.78420(10) 0.0257(5) Uani 1 1 d .
H2 H -0.1121 0.5636 0.8071 0.031 Uiso 1 1 calc R
C3 C -0.03307(12) 0.6825(2) 0.76725(10) 0.0303(5) Uani 1 1 d .
H3 H -0.0547 0.7645 0.7791 0.036 Uiso 1 1 calc R
C4 C -0.12405(11) 0.28393(19) 0.80882(9) 0.0206(4) Uani 1 1 d .
C5 C -0.19676(11) 0.2908(2) 0.77944(9) 0.0227(4) Uani 1 1 d .
C6 C -0.26239(12) 0.2683(2) 0.81200(9) 0.0262(4) Uani 1 1 d .
C7 C -0.25672(12) 0.23904(19) 0.87241(9) 0.0240(4) Uani 1 1 d .
C8 C -0.18387(12) 0.2314(2) 0.89945(9) 0.0265(5) Uani 1 1 d .
C9 C -0.11623(12) 0.2535(2) 0.86852(9) 0.0252(4) Uani 1 1 d .
C10 C -0.20354(12) 0.3207(2) 0.71378(9) 0.0285(5) Uani 1 1 d .
H10 H -0.1591 0.3791 0.7041 0.034 Uiso 1 1 calc R
C11 C -0.27762(14) 0.3950(3) 0.69544(11) 0.0374(6) Uani 1 1 d .
H11A H -0.3222 0.3366 0.7001 0.056 Uiso 1 1 calc R
H11B H -0.2749 0.4222 0.6542 0.056 Uiso 1 1 calc R
H11C H -0.2831 0.4737 0.7202 0.056 Uiso 1 1 calc R
C12 C -0.19621(16) 0.1930(3) 0.67742(11) 0.0454(6) Uani 1 1 d .
H12A H -0.1487 0.1463 0.6895 0.068 Uiso 1 1 calc R
H12B H -0.1944 0.2156 0.6356 0.068 Uiso 1 1 calc R
H12C H -0.2408 0.1357 0.6839 0.068 Uiso 1 1 calc R
C13 C -0.32937(12) 0.2197(2) 0.90772(9) 0.0273(5) Uani 1 1 d .
H13 H -0.3129 0.2103 0.9500 0.033 Uiso 1 1 calc R
C14 C -0.38263(15) 0.3403(3) 0.90257(12) 0.0444(7) Uani 1 1 d .
H14A H -0.4032 0.3477 0.8621 0.067 Uiso 1 1 calc R
H14B H -0.3534 0.4207 0.9129 0.067 Uiso 1 1 calc R
H14C H -0.4254 0.3299 0.9294 0.067 Uiso 1 1 calc R
C15 C -0.37268(13) 0.0930(3) 0.88969(11) 0.0361(5) Uani 1 1 d .
H15A H -0.3890 0.0988 0.8482 0.054 Uiso 1 1 calc R
H15B H -0.4182 0.0828 0.9138 0.054 Uiso 1 1 calc R
H15C H -0.3386 0.0163 0.8955 0.054 Uiso 1 1 calc R
C16 C -0.03753(13) 0.2487(3) 0.90080(10) 0.0365(6) Uani 1 1 d .
H16 H 0.0030 0.2649 0.8713 0.044 Uiso 1 1 calc R
C17 C -0.03100(16) 0.3585(3) 0.94731(13) 0.0489(7) Uani 1 1 d .
H17A H -0.0390 0.4450 0.9285 0.073 Uiso 1 1 calc R
H17B H 0.0204 0.3558 0.9664 0.073 Uiso 1 1 calc R
H17C H -0.0703 0.3448 0.9768 0.073 Uiso 1 1 calc R
C18 C -0.02262(18) 0.1115(3) 0.92814(13) 0.0545(8) Uani 1 1 d .
H18A H -0.0616 0.0933 0.9574 0.082 Uiso 1 1 calc R
H18B H 0.0289 0.1099 0.9472 0.082 Uiso 1 1 calc R
H18C H -0.0256 0.0437 0.8973 0.082 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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 B1 N1 108.5(2) 2_556 .
N1 B1 Br1 125.75(11) 2_556 .
N1 B1 Br1 125.75(11) . .
C1 N1 B1 107.04(16) . .
C1 N1 C4 120.72(15) . .
B1 N1 C4 132.22(17) . .
C2 C1 C1 121.27(11) . 2_556
C2 C1 N1 130.03(18) . .
C1 C1 N1 108.69(10) 2_556 .
C1 C2 C3 117.77(18) . .
C2 C3 C3 120.94(12) . 2_556
C9 C4 C5 122.08(17) . .
C9 C4 N1 119.36(18) . .
C5 C4 N1 118.53(17) . .
C6 C5 C4 118.11(18) . .
C6 C5 C10 120.90(18) . .
C4 C5 C10 120.99(17) . .
C5 C6 C7 121.34(19) . .
C8 C7 C6 118.66(18) . .
C8 C7 C13 120.81(18) . .
C6 C7 C13 120.52(19) . .
C7 C8 C9 122.02(19) . .
C4 C9 C8 117.78(19) . .
C4 C9 C16 122.20(18) . .
C8 C9 C16 119.98(19) . .
C5 C10 C11 113.68(17) . .
C5 C10 C12 110.89(19) . .
C11 C10 C12 110.2(2) . .
C7 C13 C14 111.31(18) . .
C7 C13 C15 111.77(17) . .
C14 C13 C15 110.7(2) . .
C9 C16 C17 110.8(2) . .
C9 C16 C18 111.1(2) . .
C17 C16 C18 111.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 B1 1.922(3) .
B1 N1 1.422(2) 2_556
B1 N1 1.422(2) .
N1 C1 1.411(2) .
N1 C4 1.446(2) .
C1 C2 1.387(3) .
C1 C1 1.403(4) 2_556
C2 C3 1.395(3) .
C3 C3 1.410(4) 2_556
C4 C9 1.396(3) .
C4 C5 1.410(3) .
C5 C6 1.396(3) .
C5 C10 1.526(3) .
C6 C7 1.407(3) .
C7 C8 1.390(3) .
C7 C13 1.527(3) .
C8 C9 1.404(3) .
C9 C16 1.530(3) .
C10 C11 1.533(3) .
C10 C12 1.539(4) .
C13 C14 1.530(3) .
C13 C15 1.531(3) .
C16 C17 1.534(4) .
C16 C18 1.536(4) .
