#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:25:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178715 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/26/4082678.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_4082678
loop_
_publ_author_name
'Seven, Ömer'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Wagner, Matthias'
_publ_section_title
;
 High-Yield Syntheses and Reactivity Studies of 1,2-Diborylated and
 1,2,4,5-Tetraborylated Benzenes
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1291
_journal_paper_doi               10.1021/om500104w
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C18 H26 B2 Br2 O4'
_chemical_formula_sum            'C18 H26 B2 Br2 O4'
_chemical_formula_weight         487.83
_chemical_name_systematic        ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 103.828(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2672(6)
_cell_length_b                   10.1847(5)
_cell_length_c                   14.9040(13)
_cell_measurement_reflns_used    11148
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      3.5
_cell_volume                     1071.14(14)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10795
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.803
_exptl_absorpt_correction_T_max  0.3259
_exptl_absorpt_correction_T_min  0.2737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0502
_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)+(0.0652P)²+3.7804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                1695
_reflns_number_total             1891
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om500104w_si_001.cif
_cod_data_source_block           wa1270
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4082678
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.12594(7) 1.18796(5) 0.45886(4) 0.0422(2) Uani 1 1 d .
B1 B 0.4728(7) 0.7558(5) 0.6081(3) 0.0283(10) Uani 1 1 d .
C1 C 0.3489(6) 1.0840(4) 0.4829(3) 0.0264(9) Uani 1 1 d .
C2 C 0.3434(6) 0.9702(4) 0.5322(3) 0.0281(9) Uani 1 1 d .
H2 H 0.2336 0.9513 0.5540 0.034 Uiso 1 1 calc R
C3 C 0.4950(6) 0.8819(4) 0.5511(3) 0.0257(9) Uani 1 1 d .
O12 O 0.5975(8) 0.6589(4) 0.6312(4) 0.0817(18) Uani 1 1 d .
C13 C 0.5253(13) 0.5727(9) 0.6946(8) 0.107(4) Uani 1 1 d .
C14 C 0.3311(11) 0.6049(7) 0.6798(6) 0.071(2) Uani 1 1 d .
O15 O 0.3175(6) 0.7372(4) 0.6398(4) 0.0650(14) Uani 1 1 d .
C16 C 0.6044(14) 0.4438(8) 0.6939(8) 0.109(4) Uani 1 1 d .
H16A H 0.7430 0.4497 0.7094 0.163 Uiso 1 1 calc R
H16B H 0.5602 0.4051 0.6323 0.163 Uiso 1 1 calc R
H16C H 0.5640 0.3886 0.7395 0.163 Uiso 1 1 calc R
C17 C 0.5997(17) 0.6419(9) 0.8026(5) 0.109(4) Uani 1 1 d .
H17A H 0.7366 0.6290 0.8253 0.163 Uiso 1 1 calc R
H17B H 0.5336 0.6000 0.8452 0.163 Uiso 1 1 calc R
H17C H 0.5713 0.7361 0.7989 0.163 Uiso 1 1 calc R
C18 C 0.2336(16) 0.5084(8) 0.5895(7) 0.114(4) Uani 1 1 d .
H18A H 0.0963 0.5229 0.5720 0.171 Uiso 1 1 calc R
H18B H 0.2594 0.4162 0.6067 0.171 Uiso 1 1 calc R
H18C H 0.2881 0.5299 0.5372 0.171 Uiso 1 1 calc R
C19 C 0.2106(11) 0.5965(8) 0.7462(5) 0.071(2) Uani 1 1 d .
H19A H 0.0806 0.6216 0.7156 0.107 Uiso 1 1 calc R
H19B H 0.2595 0.6560 0.7981 0.107 Uiso 1 1 calc R
H19C H 0.2117 0.5063 0.7692 0.107 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
O12 B1 O15 112.6(4) . .
O12 B1 C3 126.6(4) . .
O15 B1 C3 120.8(4) . .
C2 C1 C3 122.3(4) . 3_676
C2 C1 Br1 115.9(3) . .
C3 C1 Br1 121.7(3) 3_676 .
C1 C2 C3 121.8(4) . .
C1 C2 H2 119.1 . .
C3 C2 H2 119.1 . .
C1 C3 C2 116.0(4) 3_676 .
C1 C3 B1 126.8(4) 3_676 .
C2 C3 B1 117.2(4) . .
B1 O12 C13 106.5(5) . .
C14 C13 C16 126.7(9) . .
C14 C13 O12 104.8(6) . .
C16 C13 O12 109.6(7) . .
C14 C13 C17 97.5(8) . .
C16 C13 C17 110.2(9) . .
O12 C13 C17 106.0(7) . .
C13 C14 O15 104.2(5) . .
C13 C14 C19 127.8(7) . .
O15 C14 C19 109.5(6) . .
C13 C14 C18 101.7(8) . .
O15 C14 C18 103.7(6) . .
C19 C14 C18 107.4(7) . .
B1 O15 C14 107.1(4) . .
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C13 C17 H17A 109.5 . .
C13 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C13 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C14 C18 H18A 109.5 . .
C14 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C14 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C14 C19 H19A 109.5 . .
C14 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C14 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.897(4) .
B1 O12 1.329(7) .
B1 O15 1.337(7) .
B1 C3 1.569(6) .
C1 C2 1.378(6) .
C1 C3 1.392(6) 3_676
C2 C3 1.398(7) .
C2 H2 0.9500 .
C3 C1 1.392(6) 3_676
O12 C13 1.476(8) .
C13 C14 1.414(11) .
C13 C16 1.434(11) .
C13 C17 1.722(15) .
C14 O15 1.467(7) .
C14 C19 1.472(9) .
C14 C18 1.680(12) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C3 C1 C2 C3 0.0(7) 3_676 .
Br1 C1 C2 C3 177.1(3) . .
C1 C2 C3 C1 0.0(7) . 3_676
C1 C2 C3 B1 179.8(4) . .
O12 B1 C3 C1 -2.0(8) . 3_676
O15 B1 C3 C1 177.4(5) . 3_676
O12 B1 C3 C2 178.2(6) . .
O15 B1 C3 C2 -2.4(7) . .
O15 B1 O12 C13 -7.0(9) . .
C3 B1 O12 C13 172.5(7) . .
B1 O12 C13 C14 18.5(10) . .
B1 O12 C13 C16 157.2(9) . .
B1 O12 C13 C17 -83.9(8) . .
C16 C13 C14 O15 -151.0(10) . .
O12 C13 C14 O15 -21.9(10) . .
C17 C13 C14 O15 86.9(6) . .
C16 C13 C14 C19 79.9(15) . .
O12 C13 C14 C19 -151.0(8) . .
C17 C13 C14 C19 -42.3(10) . .
C16 C13 C14 C18 -43.4(12) . .
O12 C13 C14 C18 85.7(8) . .
C17 C13 C14 C18 -165.5(5) . .
O12 B1 O15 C14 -7.1(8) . .
C3 B1 O15 C14 173.4(5) . .
C13 C14 O15 B1 18.5(9) . .
C19 C14 O15 B1 158.0(6) . .
C18 C14 O15 B1 -87.6(7) . .
