#------------------------------------------------------------------------------
#$Date: 2019-11-17 12:23:12 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/59/7045952.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_7045952
loop_
_publ_author_name
'Oschmann, W.'
'Borner, C.'
'Kleeberg, C.'
_publ_section_title
;
 Unsymmetrical diborane(4) derivatives by copper mediated B-B coupling.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5318
_journal_page_last               5327
_journal_paper_doi               10.1039/c8dt00627j
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C10 H14 B2 N2 O2'
_chemical_formula_sum            'C10 H14 B2 N2 O2'
_chemical_formula_weight         215.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-30 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.126(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2394(4)
_cell_length_b                   12.5205(7)
_cell_length_c                   12.8693(7)
_cell_measurement_reflns_used    4907
_cell_measurement_temperature    250.1(2)
_cell_measurement_theta_max      75.2760
_cell_measurement_theta_min      4.9690
_cell_volume                     1131.21(11)
_computing_cell_refinement
;
 CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
;
_computing_data_collection
;
 CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction
;
 CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
;
_computing_molecular_graphics
;
 K. Brandenburg, 2017, Diamond 4.4.1, Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material
;
 WinGX v2014.1 (L. J. Farrugia, J. Appl. Cryst., 2012, 45, 849-854.)
;
_computing_structure_refinement
;
 SHELXL-2017/1 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3--8)
;
_computing_structure_solution
;
 SHELXT (Ver. 2014/5) (G. M. Sheldrick, Acta Cryst., 2015, A71, 3--8)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3543
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Nova'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1271
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.138
_diffrn_reflns_theta_min         5.004
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       'fragment of block'
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method
;
 Evaporation of THF solution at ambient temperature.
;
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0827P)²+0.1511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1300
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1091
_reflns_number_total             1271
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt00627j2.cif
_cod_data_source_block           wo16wo1_250K
_cod_depositor_comments
'Adding full bibliography for 7045941--7045953.cif.'
_cod_database_code               7045952
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_res_file
;

    shelx.res created by SHELXL-2014/7

TITL wo16wo1_250K in I2/a
CELL  1.54184   7.2394  12.5205  12.8693   90.000  104.126   90.000
ZERR     4.00   0.0004   0.0007   0.0007    0.000    0.006    0.000
LATT   2
SYMM  1/2 - X,   Y, - Z
SFAC  C    H    B    N    O
UNIT  40 56 8 8 8
MERG   0
FMAP   2
PLAN    5
ACTA
BOND
CONF
L.S.   4
TEMP   -23.00
WGHT    0.082700    0.151100
BASF   0.04852
FVAR       4.00939
O1    5    0.245895    0.653417    0.588271    11.00000    0.06954    0.05817 =
         0.03819   -0.00059    0.01732   -0.00073
N1    4    0.284385    0.387879    0.417797    11.00000    0.07371    0.06064 =
         0.04037   -0.00214    0.02147   -0.00037
C1    1    0.247938    0.757512    0.553651    11.00000    0.05656    0.05663 =
         0.04093    0.00125    0.01342   -0.00089
C4    1    0.250106    0.276556    0.440766    11.00000    0.06380    0.06104 =
         0.05767   -0.00599    0.02089   -0.00191
AFIX  23
H4A   2    0.351239    0.230379    0.427506    11.00000   -1.20000
H4B   2    0.127330    0.252025    0.396646    11.00000   -1.20000
AFIX   0
C2    1    0.245929    0.850268    0.609917    11.00000    0.07798    0.06509 =
         0.04554   -0.00539    0.01917   -0.00272
AFIX  43
H2    2    0.243446    0.849932    0.682605    11.00000   -1.20000
AFIX   0
C5    1    0.286630    0.414587    0.308766    11.00000    0.08557    0.08080 =
         0.04027   -0.00297    0.02131    0.00250
AFIX 137
H5A   2    0.164260    0.397143    0.261359    11.00000   -1.50000
H5B   2    0.386012    0.374159    0.287844    11.00000   -1.50000
H5C   2    0.311124    0.490371    0.303974    11.00000   -1.50000
AFIX   0
C3    1    0.247763    0.944870    0.553640    11.00000    0.10321    0.05906 =
         0.06011   -0.00476    0.02662   -0.00185
AFIX  43
H3    2    0.245934    1.010393    0.589031    11.00000   -1.20000
AFIX   0
B1    3    0.250000    0.589343    0.500000    10.50000    0.06238    0.06231 =
         0.03712    0.00000    0.01545    0.00000
B2    3    0.250000    0.454467    0.500000    10.50000    0.06014    0.05952 =
         0.03781    0.00000    0.01399    0.00000
HKLF    5

REM  wo16wo1_250K in I2/a
REM R1 =  0.0459 for    1091 Fo > 4sig(Fo)  and  0.0499 for all    1271 data
REM     76 parameters refined using      0 restraints

END

WGHT      0.0827      0.1511

REM Highest difference peak  0.161,  deepest hole -0.303,  1-sigma level  0.093
Q1    1  -0.0003  0.3325  0.3353  11.00000  0.05    0.16
Q2    1   0.5031  0.5172  0.2718  11.00000  0.05    0.16
Q3    1   0.4725  0.3965  0.2976  11.00000  0.05    0.15
Q4    1  -0.0061  0.3979  0.2355  11.00000  0.05    0.15
Q5    1   0.0204  0.2844  0.3232  11.00000  0.05    0.15
;
_shelx_res_checksum              56771
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.24589(13) 0.65342(8) 0.58827(7) 0.0546(3) Uani 1 1 d . . .
N1 N 0.28438(17) 0.38788(10) 0.41780(8) 0.0569(3) Uani 1 1 d . . .
C1 C 0.24794(18) 0.75751(11) 0.55365(10) 0.0511(4) Uani 1 1 d . . .
C4 C 0.2501(2) 0.27656(12) 0.44077(11) 0.0598(4) Uani 1 1 d . . .
H4A H 0.3512 0.2304 0.4275 0.072 Uiso 1 1 calc R U .
H4B H 0.1273 0.2520 0.3966 0.072 Uiso 1 1 calc R U .
C2 C 0.2459(2) 0.85027(13) 0.60992(11) 0.0622(4) Uani 1 1 d . . .
H2 H 0.2434 0.8499 0.6826 0.075 Uiso 1 1 calc R U .
C5 C 0.2866(2) 0.41459(14) 0.30877(10) 0.0679(4) Uani 1 1 d . . .
H5A H 0.1643 0.3971 0.2614 0.102 Uiso 1 1 calc R U .
H5B H 0.3860 0.3742 0.2878 0.102 Uiso 1 1 calc R U .
H5C H 0.3111 0.4904 0.3040 0.102 Uiso 1 1 calc R U .
C3 C 0.2478(3) 0.94487(14) 0.55364(12) 0.0730(5) Uani 1 1 d . . .
H3 H 0.2459 1.0104 0.5890 0.088 Uiso 1 1 calc R U .
B1 B 0.2500 0.58934(19) 0.5000 0.0534(5) Uani 1 2 d S T P
B2 B 0.2500 0.45447(18) 0.5000 0.0521(5) Uani 1 2 d S T P
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0695(6) 0.0582(6) 0.0382(5) -0.0006(3) 0.0173(4) -0.0007(4)
N1 0.0737(7) 0.0606(7) 0.0404(6) -0.0021(4) 0.0215(5) -0.0004(5)
C1 0.0566(7) 0.0566(8) 0.0409(7) 0.0012(5) 0.0134(5) -0.0009(5)
C4 0.0638(8) 0.0610(8) 0.0577(8) -0.0060(6) 0.0209(6) -0.0019(6)
C2 0.0780(9) 0.0651(9) 0.0455(7) -0.0054(5) 0.0192(6) -0.0027(6)
C5 0.0856(10) 0.0808(10) 0.0403(7) -0.0030(6) 0.0213(6) 0.0025(8)
C3 0.1032(12) 0.0591(8) 0.0601(9) -0.0048(7) 0.0266(8) -0.0019(8)
B1 0.0624(11) 0.0623(12) 0.0371(9) 0.000 0.0154(8) 0.000
B2 0.0601(11) 0.0595(11) 0.0378(9) 0.000 0.0140(8) 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 B1 106.03(11) . .
B2 N1 C5 129.37(13) . .
B2 N1 C4 109.98(12) . .
C5 N1 C4 117.40(12) . .
C2 C1 O1 128.90(12) . .
C2 C1 C1 122.07(8) . 2_556
O1 C1 C1 109.02(6) . 2_556
N1 C4 C4 104.14(7) . 2_556
C1 C2 C3 116.36(13) . .
C3 C3 C2 121.56(9) 2_556 .
O1 B1 O1 109.90(18) . 2_556
O1 B1 B2 125.05(9) . .
O1 B1 B2 125.05(9) 2_556 .
N1 B2 N1 107.85(18) 2_556 .
N1 B2 B1 126.08(9) 2_556 .
N1 B2 B1 126.07(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3786(16) .
O1 B1 1.3969(16) .
N1 B2 1.4159(17) .
N1 C5 1.4464(16) .
N1 C4 1.4586(19) .
C1 C2 1.3706(19) .
C1 C1 1.388(2) 2_556
C4 C4 1.525(3) 2_556
C2 C3 1.390(2) .
C3 C3 1.389(3) 2_556
B1 O1 1.3970(16) 2_556
B1 B2 1.689(3) .
B2 N1 1.4158(17) 2_556
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
B1 O1 C1 C2 -179.84(13) . .
B1 O1 C1 C1 0.34(16) . 2_556
B2 N1 C4 C4 -16.52(17) . 2_556
C5 N1 C4 C4 -178.10(13) . 2_556
O1 C1 C2 C3 -179.64(14) . .
C1 C1 C2 C3 0.2(3) 2_556 .
C1 C2 C3 C3 -0.3(3) . 2_556
C1 O1 B1 O1 -0.13(6) . 2_556
C1 O1 B1 B2 179.87(6) . .
C5 N1 B2 N1 165.42(16) . 2_556
C4 N1 B2 N1 6.71(7) . 2_556
C5 N1 B2 B1 -14.58(16) . .
C4 N1 B2 B1 -173.29(7) . .
O1 B1 B2 N1 10.73(8) . 2_556
O1 B1 B2 N1 -169.27(8) 2_556 2_556
O1 B1 B2 N1 -169.27(8) . .
O1 B1 B2 N1 10.73(8) 2_556 .
