data_21_18srv020
_audit_creation_date              2018-01-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number      '2017/1'
_publ_requested_journal           'J.Org.Chem.'
_publ_section_title
;
A Convenient Method for DFT Calculations of 
¹¹B NMR Shifts of Organoboron Compounds
;
_publ_contact_author_name         'Andrew Whiting'
_publ_contact_author_address
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
_publ_contact_author_email        'andy.whiting@durham.ac.uk'


_publ_contact_letter
;
The CIF file contains data for the structure 21 from
the paper 

"A Convenient Method for DFT Calculations of 
¹¹B NMR Shifts of Organoboron Compounds"


by H.S.Rzepa, S.Arkhipenko, E.Wang, A.S.Batsanov, M.T.Sabatini, V.Karaluka,
A.Whiting and T.D.Sheppard 

The paper will be submitted to J.Org.Chem. shortly. 
;

loop_
_publ_author_name
_publ_author_address
'Rzepa, Henry S.'
;
Department of Chemistry
Imperial College London
South Kensington Campus
London
SW7 2AZ
UK
;
'Arkhipenko, Sergey'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
'Wang, Emily'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
'Batsanov, Andrei S.'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
'Sabatini, Marco T.'
;
Department of Chemistry
University College London
Gordon St.
London
WS1H 0AJ
UK
;
'Karaluka, Valerija'
;
Department of Chemistry
University College London
Gordon St.
London
WS1H 0AJ
UK
;
'Whiting, Andrew'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
'Sheppard, Tom D.'
;
Department of Chemistry
University College London
Gordon St.
London
WS1H 0AJ
UK
;


_chemical_name_common             ?
_chemical_name_systematic         '2,7-Methoxy-1,8-diboronaphtalene'
_chemical_formula_moiety          'C12 H12 B2 O5'
_chemical_formula_sum             'C12 H12 B2 O5'
_chemical_formula_weight          257.84
_chemical_melting_point           ?
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'

_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.
;
_space_group_crystal_system       'orthorhombic'
_space_group_IT_number            61
_space_group_name_H-M_alt         'P b c a'
_space_group_name_Hall            '-P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 '-x-1/2, y-1/2, z'
 'x, -y-1/2, z-1/2'

_cell_length_a                    12.4294(6)
_cell_length_b                    12.3804(6)
_cell_length_c                    15.3932(7)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2368.72(19)
_cell_formula_units_Z             8
_cell_measurement_reflns_used     9395
_cell_measurement_temperature     120.0
_cell_measurement_theta_max       30.70
_cell_measurement_theta_min       2.65
_shelx_estimated_absorpt_T_max    0.995
_shelx_estimated_absorpt_T_min    0.987
_exptl_absorpt_coefficient_mu     0.108
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_correction_T_min   0.9413
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0592 before and 0.0445 after correction. 
The Ratio of minimum to maximum transmission is 0.9413. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'clear colourless'
_exptl_crystal_colour_lustre      clear
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.446
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        prism
_exptl_crystal_F_000              1072
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.11
_exptl_crystal_size_min           0.05
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0562
_diffrn_reflns_av_unetI/netI      0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_number             46156
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          28.998
_diffrn_reflns_theta_min          2.673
_diffrn_ambient_temperature       120.0
_diffrn_detector                  'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean  10.4
_diffrn_detector_type             'CMOS sensor'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device        '3-circle diffractometer'
_diffrn_measurement_device_type   'Bruker D8 Venture'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_radiation_monochromator   'focusing mirrors'
_diffrn_radiation_probe           X-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'microfocus sealed X-ray tube'
_diffrn_source_type               'Incoatec I\mS microsource'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 2297
_reflns_number_total              3142
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing.bruker_data_scaling    'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection        'APEX3 v.2017.3_0 (Bruker, 2017)'
_computing_data_reduction         'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'XS (Sheldrick, 2008)'
_refine_diff_density_max          0.393
_refine_diff_density_min          -0.235
_refine_diff_density_rms          0.053
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.034
_refine_ls_hydrogen_treatment     refall
_refine_ls_matrix_type            full
_refine_ls_number_parameters      220
_refine_ls_number_reflns          3142
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0648
_refine_ls_R_factor_gt            0.0419
_refine_ls_restrained_S_all       1.034
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0580P)²+0.7800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1011
_refine_ls_wR_factor_ref          0.1122
_refine_special_details           ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens    difmap
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
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
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 1.02378(8) 0.61271(7) 0.69820(5) 0.0201(2) Uani 1 1 d . . . . .
 O2 O 0.95907(9) 0.46162(8) 0.76804(6) 0.0264(3) Uani 1 1 d . . . . .
 O3 O 1.10842(8) 0.76334(8) 0.64180(6) 0.0206(2) Uani 1 1 d . . . . .
 O4 O 0.81307(8) 0.34772(8) 0.67506(6) 0.0230(2) Uani 1 1 d . . . . .
 O5 O 1.05245(8) 0.81309(7) 0.47831(6) 0.0224(2) Uani 1 1 d . . . . .
 C1 C 0.88913(10) 0.50170(10) 0.61226(7) 0.0153(3) Uani 1 1 d . . . . .
 C2 C 0.81875(10) 0.41521(11) 0.60477(8) 0.0176(3) Uani 1 1 d . . . . .
 C3 C 0.75863(11) 0.39555(12) 0.52848(8) 0.0211(3) Uani 1 1 d . . . . .
 C4 C 0.76951(10) 0.46464(12) 0.45955(8) 0.0209(3) Uani 1 1 d . . . . .
 C5 C 0.83874(10) 0.55465(11) 0.46298(8) 0.0173(3) Uani 1 1 d . . . . .
 C6 C 0.85104(11) 0.62631(12) 0.39218(8) 0.0204(3) Uani 1 1 d . . . . .
 C7 C 0.91973(11) 0.71208(11) 0.39557(8) 0.0200(3) Uani 1 1 d . . . . .
 C8 C 0.98069(10) 0.72948(10) 0.47210(8) 0.0170(3) Uani 1 1 d . . . . .
 C9 C 0.97252(10) 0.66258(10) 0.54392(8) 0.0151(3) Uani 1 1 d . . . . .
 C10 C 0.90013(10) 0.57303(10) 0.53988(7) 0.0143(3) Uani 1 1 d . . . . .
 C11 C 0.73367(14) 0.26481(13) 0.67661(10) 0.0293(3) Uani 1 1 d . . . . .
 C12 C 1.04977(15) 0.89617(13) 0.41319(10) 0.0292(3) Uani 1 1 d . . . . .
 B1 B 0.95811(12) 0.52276(12) 0.69542(9) 0.0181(3) Uani 1 1 d . . . . .
 B2 B 1.03826(12) 0.68128(12) 0.62911(9) 0.0157(3) Uani 1 1 d . . . . .
 H2 H 0.9202(16) 0.4051(16) 0.7657(13) 0.045(6) Uiso 1 1 d . . . . .
 H3 H 1.1143(16) 0.8005(16) 0.5954(13) 0.049(6) Uiso 1 1 d . . . . .
 H3A H 0.7121(14) 0.3345(13) 0.5240(11) 0.033(5) Uiso 1 1 d . . . . .
 H4 H 0.7283(14) 0.4531(13) 0.4062(11) 0.032(5) Uiso 1 1 d . . . . .
 H6 H 0.8097(13) 0.6122(12) 0.3391(10) 0.024(4) Uiso 1 1 d . . . . .
 H7 H 0.9294(13) 0.7593(13) 0.3481(11) 0.027(4) Uiso 1 1 d . . . . .
 H11A H 0.7450(14) 0.2135(13) 0.6281(11) 0.031(4) Uiso 1 1 d . . . . .
 H11B H 0.6617(15) 0.2960(14) 0.6728(11) 0.036(5) Uiso 1 1 d . . . . .
 H11C H 0.7457(14) 0.2266(14) 0.7314(12) 0.038(5) Uiso 1 1 d . . . . .
 H12A H 1.0686(14) 0.8667(14) 0.3571(12) 0.034(4) Uiso 1 1 d . . . . .
 H12B H 1.1014(15) 0.9500(14) 0.4332(12) 0.038(5) Uiso 1 1 d . . . . .
 H12C H 0.9751(16) 0.9305(14) 0.4104(12) 0.042(5) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 B1 1.3814(17) . ?
 O1 B2 1.3727(17) . ?
 O2 B1 1.3502(17) . ?
 O2 H2 0.85(2) . ?
 O3 B2 1.3531(17) . ?
 O3 H3 0.85(2) . ?
 O4 C2 1.3689(16) . ?
 O4 C11 1.4242(17) . ?
 O5 C8 1.3697(16) . ?
 O5 C12 1.4367(16) . ?
 C1 C2 1.3875(18) . ?
 C1 C10 1.4283(17) . ?
 C1 B1 1.5625(18) . ?
 C2 C3 1.4131(17) . ?
 C3 C4 1.369(2) . ?
 C3 H3A 0.955(17) . ?
 C4 C5 1.4090(19) . ?
 C4 H4 0.979(17) . ?
 C5 C6 1.4135(19) . ?
 C5 C10 1.4266(16) . ?
 C6 C7 1.364(2) . ?
 C6 H6 0.981(16) . ?
 C7 C8 1.4171(17) . ?
 C7 H7 0.943(17) . ?
 C8 C9 1.3851(17) . ?
 C9 C10 1.4292(17) . ?
 C9 B2 1.5623(18) . ?
 C11 H11A 0.991(17) . ?
 C11 H11B 0.975(19) . ?
 C11 H11C 0.978(19) . ?
 C12 H12A 0.966(19) . ?
 C12 H12B 0.975(19) . ?
 C12 H12C 1.021(19) . ?

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
  _geom_angle_publ_flag
 B2 O1 B1 123.50(10) . . ?
 B1 O2 H2 114.9(13) . . ?
 B2 O3 H3 109.9(13) . . ?
 C2 O4 C11 119.27(11) . . ?
 C8 O5 C12 118.50(11) . . ?
 C2 C1 C10 118.21(11) . . ?
 C2 C1 B1 122.88(11) . . ?
 C10 C1 B1 118.90(11) . . ?
 O4 C2 C1 115.97(11) . . ?
 O4 C2 C3 121.64(12) . . ?
 C1 C2 C3 122.37(12) . . ?
 C2 C3 H3A 121.1(10) . . ?
 C4 C3 C2 118.95(13) . . ?
 C4 C3 H3A 119.9(10) . . ?
 C3 C4 C5 121.69(12) . . ?
 C3 C4 H4 120.5(10) . . ?
 C5 C4 H4 117.8(10) . . ?
 C4 C5 C6 122.25(11) . . ?
 C4 C5 C10 118.94(12) . . ?
 C6 C5 C10 118.80(12) . . ?
 C5 C6 H6 118.3(9) . . ?
 C7 C6 C5 121.80(12) . . ?
 C7 C6 H6 119.9(9) . . ?
 C6 C7 C8 119.01(12) . . ?
 C6 C7 H7 122.2(10) . . ?
 C8 C7 H7 118.8(10) . . ?
 O5 C8 C7 121.41(11) . . ?
 O5 C8 C9 116.35(11) . . ?
 C9 C8 C7 122.23(12) . . ?
 C8 C9 C10 118.38(11) . . ?
 C8 C9 B2 122.89(11) . . ?
 C10 C9 B2 118.74(11) . . ?
 C1 C10 C9 120.39(11) . . ?
 C5 C10 C1 119.83(11) . . ?
 C5 C10 C9 119.78(11) . . ?
 O4 C11 H11A 110.6(10) . . ?
 O4 C11 H11B 110.4(11) . . ?
 O4 C11 H11C 104.9(10) . . ?
 H11A C11 H11B 109.8(14) . . ?
 H11A C11 H11C 108.5(14) . . ?
 H11B C11 H11C 112.6(15) . . ?
 O5 C12 H12A 110.3(10) . . ?
 O5 C12 H12B 104.7(11) . . ?
 O5 C12 H12C 110.4(10) . . ?
 H12A C12 H12B 112.4(15) . . ?
 H12A C12 H12C 109.9(15) . . ?
 H12B C12 H12C 109.1(14) . . ?
 O1 B1 C1 118.96(11) . . ?
 O2 B1 O1 114.90(11) . . ?
 O2 B1 C1 126.13(12) . . ?
 O1 B2 C9 119.35(11) . . ?
 O3 B2 O1 115.91(11) . . ?
 O3 B2 C9 124.72(12) . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
  _geom_hbond_publ_flag
 O2 H2 O4 0.85(2) 2.06(2) 2.7074(14) 132.9(17) . yes
 O3 H3 O5 0.85(2) 1.97(2) 2.6826(13) 141.0(18) . yes

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_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 C1 C2 O4 C11 172.58(12) . . . . ?
 C2 C1 B1 O1 -178.12(12) . . . . ?
 C2 C1 B1 O2 0.5(2) . . . . ?
 C3 C2 O4 C11 -9.22(19) . . . . ?
 C7 C8 O5 C12 12.50(18) . . . . ?
 C8 C9 B2 O1 178.51(12) . . . . ?
 C8 C9 B2 O3 0.3(2) . . . . ?
 C9 C8 O5 C12 -168.45(12) . . . . ?
 C10 C1 B1 O1 3.15(18) . . . . ?
 C10 C1 B1 O2 -178.23(13) . . . . ?
 C10 C9 B2 O1 -1.03(18) . . . . ?
 C10 C9 B2 O3 -179.26(12) . . . . ?
 B1 O1 B2 O3 -177.66(12) . . . . ?
 B1 O1 B2 C9 3.96(19) . . . . ?
 B2 O1 B1 O2 176.24(12) . . . . ?
 B2 O1 B1 C1 -4.98(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
