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#$Date: 2016-03-26 03:23:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180180 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/76/7107623.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_7107623
loop_
_publ_author_name
'Merle Arrowsmith'
'Terrance J. Hadlington'
'Michael S. Hill'
'Gabriele Kociok-Kohn'
_publ_section_title
;
 Magnesium-catalysed hydroboration of aldehydes and ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              4567
_journal_paper_doi               10.1039/c2cc30565h
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C26 H36 B2 O6'
_chemical_formula_sum            'C26 H36 B2 O6'
_chemical_formula_weight         466.17
_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                 102.8300(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2719(2)
_cell_length_b                   9.9302(2)
_cell_length_c                   15.8441(3)
_cell_measurement_reflns_used    22947
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1268.97(5)
_computing_cell_refinement       'HKL Scalepack (Otwinski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
DENZO-SCALEPACK Z. Otwinowski and W. Minor, "
Processing of X-ray Diffraction Data Collected in Oscillation Mode ",
Methods in Enzymology, Volume 276: Macromolecular Crystallography,
part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
'WinGX publication routines, Farrugia,
L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_computing_structure_refinement
;
SHELXL97 -Program for Crystal Structure Analysis (Release 97-2).
Sheldrick, G.M., Institut für Anorganische Chemie der Universität,
Tammanstrasse 4, D-3400 Göttingen, Germany, 1998
;
_computing_structure_solution
;
SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. ,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
(1999) J. Appl. Cryst. 32, 115-119
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '298 2.0 degree images with φ and ω scans'
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21410
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.53
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9516
_exptl_absorpt_correction_T_min  0.9516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0469
_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)+(0.0537P)²+0.5950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1233
_reflns_number_gt                2576
_reflns_number_total             2878
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc30565h.txt
_cod_data_source_block           k11msh12
_cod_database_code               7107623
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
B B 0.07330(18) 0.32206(15) 0.37428(9) 0.0253(3) Uani 1 1 d .
O1 O -0.03848(13) 0.36742(10) 0.30336(6) 0.0326(2) Uani 1 1 d .
O2 O 0.13296(12) 0.19606(10) 0.36734(6) 0.0319(2) Uani 1 1 d .
O3 O 0.12902(11) 0.39572(9) 0.44820(6) 0.0267(2) Uani 1 1 d .
C1 C -0.08103(18) 0.25137(13) 0.24523(8) 0.0292(3) Uani 1 1 d .
C2 C -0.2430(2) 0.19490(19) 0.26042(11) 0.0438(4) Uani 1 1 d .
H2A H -0.2281 0.1679 0.3212 0.066 Uiso 1 1 calc R
H2B H -0.2758 0.1164 0.2230 0.066 Uiso 1 1 calc R
H2C H -0.3295 0.2640 0.2469 0.066 Uiso 1 1 calc R
C3 C -0.1040(3) 0.30014(17) 0.15258(10) 0.0454(4) Uani 1 1 d .
H3A H -0.1933 0.3670 0.1404 0.068 Uiso 1 1 calc R
H3B H -0.1327 0.2237 0.1129 0.068 Uiso 1 1 calc R
H3C H -0.0007 0.3412 0.1445 0.068 Uiso 1 1 calc R
C4 C 0.07039(19) 0.15511(15) 0.27756(9) 0.0323(3) Uani 1 1 d .
C5 C 0.0233(3) 0.00715(17) 0.27851(12) 0.0544(5) Uani 1 1 d .
H5A H 0.1232 -0.0468 0.3000 0.082 Uiso 1 1 calc R
H5B H -0.0293 -0.0217 0.2197 0.082 Uiso 1 1 calc R
H5C H -0.0543 -0.0054 0.3164 0.082 Uiso 1 1 calc R
C6 C 0.2103(3) 0.1741(3) 0.23158(13) 0.0597(5) Uani 1 1 d .
H6A H 0.2364 0.2702 0.2297 0.090 Uiso 1 1 calc R
H6B H 0.1768 0.1392 0.1724 0.090 Uiso 1 1 calc R
H6C H 0.3085 0.1252 0.2627 0.090 Uiso 1 1 calc R
C7 C 0.04582(15) 0.51606(12) 0.46368(8) 0.0231(3) Uani 1 1 d .
H7 H -0.0368 0.5418 0.4099 0.028 Uiso 1 1 calc R
C8 C 0.17081(16) 0.62884(13) 0.48870(8) 0.0235(3) Uani 1 1 d .
C9 C 0.33421(16) 0.60090(14) 0.52991(9) 0.0279(3) Uani 1 1 d .
H9 H 0.3682 0.5103 0.5421 0.033 Uiso 1 1 calc R
C10 C 0.44811(18) 0.70491(16) 0.55329(9) 0.0333(3) Uani 1 1 d .
H10 H 0.5595 0.6848 0.5811 0.040 Uiso 1 1 calc R
C11 C 0.40007(19) 0.83722(15) 0.53632(9) 0.0352(3) Uani 1 1 d .
H11 H 0.4781 0.9079 0.5528 0.042 Uiso 1 1 calc R
C12 C 0.2377(2) 0.86664(15) 0.49518(9) 0.0359(3) Uani 1 1 d .
H12 H 0.2044 0.9575 0.4832 0.043 Uiso 1 1 calc R
C13 C 0.12323(18) 0.76234(14) 0.47143(9) 0.0304(3) Uani 1 1 d .
H13 H 0.0121 0.7826 0.4433 0.036 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'
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
O2 B O1 115.45(12) . .
O2 B O3 120.08(12) . .
O1 B O3 124.45(12) . .
B O1 C1 106.37(10) . .
B O2 C4 106.19(11) . .
B O3 C7 120.67(10) . .
O1 C1 C3 108.51(11) . .
O1 C1 C2 106.69(11) . .
C3 C1 C2 110.22(13) . .
O1 C1 C4 102.16(10) . .
C3 C1 C4 115.45(12) . .
C2 C1 C4 113.05(12) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
O2 C4 C6 106.95(13) . .
O2 C4 C5 107.20(12) . .
C6 C4 C5 110.53(15) . .
O2 C4 C1 103.48(10) . .
C6 C4 C1 114.11(14) . .
C5 C4 C1 113.85(13) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O3 C7 C8 109.67(10) . .
O3 C7 C7 106.86(12) . 3_566
C8 C7 C7 112.12(12) . 3_566
O3 C7 H7 109.4 . .
C8 C7 H7 109.4 . .
C7 C7 H7 109.4 3_566 .
C9 C8 C13 118.98(12) . .
C9 C8 C7 120.68(12) . .
C13 C8 C7 120.35(12) . .
C10 C9 C8 120.42(13) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C11 C10 C9 120.36(14) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C12 119.88(13) . .
C10 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
C11 C12 C13 119.85(14) . .
C11 C12 H12 120.1 . .
C13 C12 H12 120.1 . .
C8 C13 C12 120.51(13) . .
C8 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B O2 1.3584(18) .
B O1 1.3634(18) .
B O3 1.3709(17) .
O1 C1 1.4684(15) .
O2 C4 1.4595(16) .
O3 C7 1.4272(15) .
C1 C3 1.5172(19) .
C1 C2 1.520(2) .
C1 C4 1.568(2) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 C6 1.510(2) .
C4 C5 1.521(2) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.5160(17) .
C7 C7 1.546(2) 3_566
C7 H7 1.0000 .
C8 C9 1.3922(19) .
C8 C13 1.3926(19) .
C9 C10 1.3917(19) .
C9 H9 0.9500 .
C10 C11 1.382(2) .
C10 H10 0.9500 .
C11 C12 1.388(2) .
C11 H11 0.9500 .
C12 C13 1.397(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
