#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:47:02 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180276 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/62/7116290.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_7116290
loop_
_publ_author_name
'Del Grosso, Alessandro'
'Ayuso Carrillo, Josue'
'Ingleson, Michael J.'
_publ_section_title
;
 Regioselective electrophilic borylation of haloarenes.
;
_journal_issue                   14
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2878
_journal_paper_doi               10.1039/c4cc10153g
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C12 H15 B Cl F O2'
_chemical_formula_sum            'C12 H15 B Cl F O2'
_chemical_formula_weight         256.50
_chemical_name_systematic
;
2-(4-chloro-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2014-12-10 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.422(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8661(7)
_cell_length_b                   7.5020(4)
_cell_length_c                   12.4291(8)
_cell_measurement_reflns_used    1463
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.7100
_cell_measurement_theta_min      3.5370
_cell_volume                     1291.76(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9955
_diffrn_measured_fraction_theta_max 0.8590
_diffrn_measurement_details
;
  1 omega  -94.00   10.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      -20.4767  -37.0000 -150.0000 104

  2 omega  -25.00   55.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      -20.4767   19.0000   30.0000 80

  3 omega  -45.00    0.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -       21.6485  -57.0000  120.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0438674000
_diffrn_orient_matrix_UB_12      0.0102686000
_diffrn_orient_matrix_UB_13      -0.0267789000
_diffrn_orient_matrix_UB_21      -0.0184841000
_diffrn_orient_matrix_UB_22      0.0781694000
_diffrn_orient_matrix_UB_23      -0.0255396000
_diffrn_orient_matrix_UB_31      0.0189672000
_diffrn_orient_matrix_UB_32      0.0521257000
_diffrn_orient_matrix_UB_33      0.0434723000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5252
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.861
_diffrn_reflns_theta_min         3.281
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       irregular
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0547
_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)+(0.0367P)²+0.4215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2005
_reflns_number_total             2898
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4cc10153g2.cif
_cod_data_source_block           amji207
_cod_depositor_comments
'Adding full bibliography for 7116287--7116290.cif.'
_cod_original_cell_volume        1291.77(12)
_cod_database_code               7116290
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         C12H15B1Cl1F1O2
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C5(H5)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C11(H11a,H11b,H11c), C8(H8a,H8b,H8c), C12(H12a,H12b,H12c)
;
_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.
;
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
Cl1 Cl -0.00803(5) 0.48667(9) 0.28782(6) 0.0402(2) Uani 1 1 d . .
F1 F 0.31237(9) 0.79076(19) 0.34140(12) 0.0352(4) Uani 1 1 d . .
C9 C 0.44325(18) 1.0453(3) 0.6785(2) 0.0357(6) Uani 1 1 d . .
H9A H 0.3993 0.9609 0.7075 0.054 Uiso 1 1 calc R U
H9B H 0.4707 1.1177 0.7356 0.054 Uiso 1 1 calc R U
H9C H 0.4938 0.9828 0.6439 0.054 Uiso 1 1 calc R U
B1 B 0.25939(18) 1.0091(3) 0.5284(2) 0.0211(6) Uani 1 1 d . .
O2 O 0.22262(10) 1.1077(2) 0.61006(13) 0.0248(4) Uani 1 1 d . .
C11 C 0.26234(18) 1.4134(3) 0.5789(2) 0.0363(7) Uani 1 1 d . .
H11A H 0.2603 1.3906 0.5028 0.054 Uiso 1 1 calc R U
H11B H 0.3073 1.5078 0.5953 0.054 Uiso 1 1 calc R U
H11C H 0.1993 1.4476 0.6005 0.054 Uiso 1 1 calc R U
C3 C 0.06906(16) 0.6319(3) 0.35816(19) 0.0253(5) Uani 1 1 d . .
C4 C 0.03671(16) 0.7231(3) 0.44659(19) 0.0267(6) Uani 1 1 d . .
H4 H -0.0254 0.7056 0.4700 0.032 Uiso 1 1 calc R U
O1 O 0.35357(10) 1.0452(2) 0.51010(12) 0.0234(4) Uani 1 1 d . .
C2 C 0.16127(17) 0.6548(3) 0.32239(19) 0.0254(5) Uani 1 1 d . .
H2 H 0.1823 0.5931 0.2629 0.031 Uiso 1 1 calc R U
C5 C 0.09950(16) 0.8413(3) 0.49927(19) 0.0240(5) Uani 1 1 d . .
H5 H 0.0782 0.9034 0.5585 0.029 Uiso 1 1 calc R U
C10 C 0.29426(16) 1.2457(3) 0.63903(19) 0.0243(5) Uani 1 1 d . .
C6 C 0.19407(15) 0.8710(3) 0.46664(18) 0.0204(5) Uani 1 1 d . .
C8 C 0.45842(17) 1.2963(3) 0.5498(2) 0.0337(6) Uani 1 1 d . .
H8A H 0.4761 1.3844 0.6031 0.051 Uiso 1 1 calc R U
H8B H 0.4274 1.3534 0.4885 0.051 Uiso 1 1 calc R U
H8C H 0.5153 1.2356 0.5279 0.051 Uiso 1 1 calc R U
C7 C 0.38960(16) 1.1628(3) 0.59701(19) 0.0239(5) Uani 1 1 d . .
C1 C 0.22063(16) 0.7723(3) 0.37797(19) 0.0240(5) Uani 1 1 d . .
C12 C 0.29392(18) 1.2746(4) 0.7595(2) 0.0359(7) Uani 1 1 d . .
H12A H 0.2314 1.3158 0.7787 0.054 Uiso 1 1 calc R U
H12B H 0.3417 1.3621 0.7803 0.054 Uiso 1 1 calc R U
H12C H 0.3084 1.1644 0.7959 0.054 Uiso 1 1 calc R U
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
Cl1 0.0425(4) 0.0396(4) 0.0381(4) -0.0112(3) -0.0030(3) -0.0147(3)
F1 0.0222(7) 0.0456(9) 0.0382(9) -0.0119(8) 0.0077(6) -0.0025(6)
C9 0.0313(13) 0.0401(15) 0.0349(16) 0.0023(14) -0.0082(12) 0.0033(11)
B1 0.0259(13) 0.0225(13) 0.0147(13) 0.0045(12) -0.0026(11) 0.0013(10)
O2 0.0230(8) 0.0267(9) 0.0248(9) -0.0067(8) 0.0024(7) -0.0066(7)
C11 0.0352(14) 0.0285(14) 0.0448(17) -0.0017(14) -0.0037(13) 0.0027(11)
C3 0.0304(12) 0.0200(12) 0.0247(13) 0.0001(11) -0.0072(10) -0.0024(9)
C4 0.0231(11) 0.0282(13) 0.0289(14) 0.0006(12) 0.0016(10) -0.0042(10)
O1 0.0204(8) 0.0264(9) 0.0235(9) -0.0039(8) 0.0014(7) -0.0021(6)
C2 0.0331(12) 0.0229(12) 0.0201(13) -0.0042(11) -0.0013(10) 0.0057(10)
C5 0.0267(11) 0.0223(12) 0.0230(13) -0.0027(11) 0.0014(10) -0.0003(9)
C10 0.0250(11) 0.0223(12) 0.0256(13) -0.0026(11) -0.0001(10) -0.0057(9)
C6 0.0251(11) 0.0188(11) 0.0170(12) 0.0013(10) -0.0029(9) 0.0024(9)
C8 0.0289(13) 0.0380(15) 0.0342(15) -0.0025(13) 0.0017(11) -0.0097(11)
C7 0.0239(11) 0.0250(12) 0.0225(13) -0.0002(11) -0.0014(10) -0.0035(9)
C1 0.0215(11) 0.0245(12) 0.0260(13) 0.0021(11) 0.0021(10) 0.0024(9)
C12 0.0380(14) 0.0426(16) 0.0271(14) -0.0119(13) 0.0032(12) -0.0102(12)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
O2 B1 C6 119.8(2)
O1 B1 O2 113.9(2)
O1 B1 C6 126.3(2)
B1 O2 C10 107.03(17)
C4 C3 Cl1 119.76(18)
C2 C3 Cl1 118.33(18)
C2 C3 C4 121.9(2)
C3 C4 C5 118.2(2)
B1 O1 C7 107.23(17)
C1 C2 C3 117.5(2)
C4 C5 C6 122.6(2)
O2 C10 C11 106.43(19)
O2 C10 C7 102.09(17)
O2 C10 C12 108.26(18)
C11 C10 C7 113.34(19)
C12 C10 C11 110.8(2)
C12 C10 C7 115.1(2)
C5 C6 B1 119.6(2)
C1 C6 B1 125.2(2)
C1 C6 C5 115.2(2)
C9 C7 C10 113.90(19)
C9 C7 C8 110.09(19)
O1 C7 C9 106.55(18)
O1 C7 C10 102.59(17)
O1 C7 C8 108.20(19)
C8 C7 C10 114.76(19)
F1 C1 C6 119.2(2)
C2 C1 F1 116.2(2)
C2 C1 C6 124.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.736(2)
F1 C1 1.376(2)
C9 C7 1.514(3)
B1 O2 1.372(3)
B1 O1 1.362(3)
B1 C6 1.557(3)
O2 C10 1.469(3)
C11 C10 1.520(3)
C3 C4 1.386(3)
C3 C2 1.382(3)
C4 C5 1.387(3)
O1 C7 1.466(3)
C2 C1 1.372(3)
C5 C6 1.407(3)
C10 C7 1.570(3)
C10 C12 1.513(3)
C6 C1 1.390(3)
C8 C7 1.519(3)
