data_global

_publ_contact_author               'Andrei S.Batsanov'
_publ_contact_author_email          a.s.batsanov@durham.ac.uk
_publ_contact_author_id_orcid       0000-0002-4912-0981

loop_
    _publ_author_name
    _publ_author_address
 'Arkhipenko, Sergey' 
; Centre for Sustainable Chemical Processes 
 Department of Chemistry, University of Durham
 South Road, Durham DH1 3LE, United Kingdom 
;
 'Batsanov, Andrei S.' 
; Department of Chemistry, University of Durham
 South Road, Durham DH1 3LE, United Kingdom 
;
 'Sabatini, Marco T.'  
; Department of Chemistry, University College London,   
 Gower Street, London WC1E 6BT, United Kingdom 
;
 'Karaluka, Valerija'  
; Department of Chemistry, University College London,   
 Gower Street, London WC1E 6BT, United Kingdom 
;
 'Sheppard, Tom D.' 
; Department of Chemistry, University College London,   
 Gower Street, London WC1E 6BT, United Kingdom 
;
 'Rzepa, Henry S.'  
; Department of Chemistry, Imperial College London  
 South Kensington Campus, London SW7 2AZ   
 United Kingdom 
;
 'Whiting, Andrew'  
; Centre for Sustainable Chemical Processes 
 Department of Chemistry, University of Durham
 South Road, Durham DH1 3LE, United Kingdom 
;
_journal_name_full                 'Chemical Science'
_journal_volume                    '?'
_journal_page_first                '?'
_journal_page_last                 '?'
_journal_year                      '2017'
_database_code_depnum_ccdc_journal  ? 

_publ_section_title
; Mechanistic insights into the boron-catalysed direct amidation reaction
;

_publ_section_references
; 
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. 

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. 

Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790;

Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984;

Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45,
 575-580.

;

#======================================================================

data_S2_16srv036 
_database_code_depnum_ccdc_archive	1563952     

_audit_creation_date              2017-07-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number      '2016/6'

_chemical_name_common             ?
_chemical_name_systematic         'Bis-(2-chlorophenyl)borinic acid ethanolamine complex'
_chemical_formula_moiety          'C14 H14 B Br0.05 Cl1.95 N O'
_chemical_formula_sum             'C14 H14 B Br0.05 Cl1.95 N O'
_chemical_formula_weight          296.19
_chemical_absolute_configuration  ad
_chemical_melting_point           487(1)
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'
 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 '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            19
_space_group_name_H-M_alt         'P 21 21 21'
_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'

_cell_length_a                    8.9466(7)
_cell_length_b                    10.7958(9)
_cell_length_c                    13.9126(12)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1343.76(19)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     9713
_cell_measurement_temperature     120
_cell_measurement_theta_max       33.37
_cell_measurement_theta_min       2.39
_shelx_estimated_absorpt_T_max    0.851
_shelx_estimated_absorpt_T_min    0.737
_exptl_absorpt_coefficient_mu     0.610
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_correction_T_min   0.9208
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1120 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.9208.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.464
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        tablet
_exptl_crystal_F_000              612
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 0.00 -1.00 -1.00 0.1660
 0.00 1.00 1.00 0.1870
 2.00 0.00 -1.00 0.1370
 -2.00 0.00 1.00 0.1050
 0.00 1.00 -1.00 0.1420
 0.00 -1.00 1.00 0.2120
 0.00 0.00 1.00 0.1870
 -1.00 0.00 2.00 0.1520
 -1.00 -1.00 2.00 0.1430

_exptl_crystal_size_max           0.533
_exptl_crystal_size_mid           0.433
_exptl_crystal_size_min           0.274
_exptl_special_details
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of narrow-frame ω-scans (scan 
width 0.5°, 5s exposure), every run at a different φ angle.
Two runs of φ-scans (scan width 1°, 1s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0301
_diffrn_reflns_av_unetI/netI      0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_h_min        -13
_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             35671
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          33.603
_diffrn_reflns_theta_min          2.388
_diffrn_ambient_temperature       120.0
_diffrn_detector_area_resol_mean  10.4
_diffrn_detector_type             'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device        '3-circle area detector 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'
_reflns_Friedel_coverage          0.771
_reflns_Friedel_fraction_full     0.999
_reflns_Friedel_fraction_max      0.995
_reflns_number_gt                 5053
_reflns_number_total              5299
_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_cell_refinement        'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection        'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction         'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL 2016/6 multi-CPU (Sheldrick, 2015)'
_computing_structure_solution     'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max          0.549
_refine_diff_density_min          -0.423
_refine_diff_density_rms          0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 2145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.027(9)
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.073
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      180
_refine_ls_number_reflns          5299
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0293
_refine_ls_R_factor_gt            0.0269
_refine_ls_restrained_S_all       1.073
_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)+(0.0410P)²+0.3170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0726
_refine_ls_wR_factor_ref          0.0741
_refine_special_details           
; Cl(1) site is contaminated with 5% of Br, refined as a single atom with 
 mixed scattering factor. Amino H atoms - refall, other H atoms - riding (constr).
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{Cl1, Br1}
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Br1)
4. Others
 Fixed Sof: Cl1(0.95) Br1(0.05)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
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
 Cl1 Cl -0.02231(4) 0.56926(3) 0.32281(3) 0.01985(8) Uani 0.95 1 d . . P A 1
 Cl2 Cl 0.26694(4) 0.93483(4) 0.45733(3) 0.02139(8) Uani 1 1 d . . . . .
 O O 0.39175(11) 0.64107(10) 0.51783(7) 0.01303(18) Uani 1 1 d . . . . .
 N N 0.12698(14) 0.68238(12) 0.52083(9) 0.0132(2) Uani 1 1 d . . . . .
 H1N H 0.087(3) 0.741(3) 0.5034(19) 0.021(6) Uiso 1 1 d . . . . .
 H2N H 0.058(3) 0.631(2) 0.5210(16) 0.014(5) Uiso 1 1 d . . . . .
 C1 C 0.33944(17) 0.62619(14) 0.61348(10) 0.0162(2) Uani 1 1 d . . . . .
 H1A H 0.413645 0.658015 0.660136 0.019 Uiso 1 1 calc R . . . .
 H1B H 0.319785 0.537821 0.627657 0.019 Uiso 1 1 calc R . . . .
 C2 C 0.19555(16) 0.70128(15) 0.61812(10) 0.0171(2) Uani 1 1 d . . . . .
 H2A H 0.128880 0.670105 0.669510 0.020 Uiso 1 1 calc R . . . .
 H2B H 0.216868 0.789986 0.629851 0.020 Uiso 1 1 calc R . . . .
 C3 C 0.22083(15) 0.48987(13) 0.42582(10) 0.0125(2) Uani 1 1 d . . . . .
 C4 C 0.09352(15) 0.45391(13) 0.37407(10) 0.0136(2) Uani 1 1 d . . . . .
 C5 C 0.05214(17) 0.33147(14) 0.35786(11) 0.0165(3) Uani 1 1 d . . . . .
 H5 H -0.036545 0.312343 0.323362 0.020 Uiso 1 1 calc R . . . .
 C6 C 0.14346(18) 0.23758(14) 0.39326(11) 0.0183(3) Uani 1 1 d . . . . .
 H6 H 0.117893 0.153236 0.382855 0.022 Uiso 1 1 calc R . . . .
 C7 C 0.27222(19) 0.26791(14) 0.44392(11) 0.0187(3) Uani 1 1 d . . . . .
 H7 H 0.335187 0.204106 0.467824 0.022 Uiso 1 1 calc R . . . .
 C8 C 0.30934(17) 0.39175(13) 0.45979(11) 0.0156(2) Uani 1 1 d . . . . .
 H8 H 0.397648 0.410380 0.494845 0.019 Uiso 1 1 calc R . . . .
 C9 C 0.29751(15) 0.71761(14) 0.35697(10) 0.0145(2) Uani 1 1 d . . . . .
 C10 C 0.30148(17) 0.84680(15) 0.35398(12) 0.0182(3) Uani 1 1 d . . . . .
 C11 C 0.33847(19) 0.91504(18) 0.27186(14) 0.0277(4) Uani 1 1 d . . . . .
 H11 H 0.338886 1.003008 0.273572 0.033 Uiso 1 1 calc R . . . .
 C12 C 0.3743(2) 0.8529(2) 0.18852(15) 0.0335(5) Uani 1 1 d . . . . .
 H12 H 0.398370 0.897967 0.131937 0.040 Uiso 1 1 calc R . . . .
 C13 C 0.3751(2) 0.7252(2) 0.18740(13) 0.0303(4) Uani 1 1 d . . . . .
 H13 H 0.401190 0.682122 0.130281 0.036 Uiso 1 1 calc R . . . .
 C14 C 0.33754(19) 0.65935(18) 0.27009(11) 0.0218(3) Uani 1 1 d . . . . .
 H14 H 0.339008 0.571412 0.267777 0.026 Uiso 1 1 calc R . . . .
 B B 0.26455(17) 0.63292(14) 0.45109(11) 0.0117(2) Uani 1 1 d . . . . .
 Br1 Br -0.02231(4) 0.56926(3) 0.32281(3) 0.01985(8) Uani 0.05 1 d . . P A 2


_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
 Cl1 C4 1.7701(14) . ?
 Cl2 C10 1.7510(18) . ?
 O C1 1.4197(18) . ?
 O B 1.4713(18) . ?
 N C2 1.5001(19) . ?
 N B 1.656(2) . ?
 C1 C2 1.523(2) . ?
 C3 C4 1.4023(19) . ?
 C3 C8 1.404(2) . ?
 C3 B 1.631(2) . ?
 C4 C5 1.391(2) . ?
 C4 Br1 1.7701(14) . ?
 C5 C6 1.392(2) . ?
 C6 C7 1.390(2) . ?
 C7 C8 1.395(2) . ?
 C9 C10 1.396(2) . ?
 C9 C14 1.409(2) . ?
 C9 B 1.624(2) . ?
 C10 C11 1.399(2) . ?
 C11 C12 1.377(3) . ?
 C12 C13 1.379(3) . ?
 C13 C14 1.393(2) . ?

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
 C1 O B 109.26(11) . . ?
 C2 N B 105.59(10) . . ?
 O C1 C2 104.97(11) . . ?
 N C2 C1 103.59(11) . . ?
 C4 C3 C8 114.96(13) . . ?
 C4 C3 B 124.57(12) . . ?
 C8 C3 B 120.41(12) . . ?
 C3 C4 Cl1 119.18(10) . . ?
 C3 C4 Br1 119.18(10) . . ?
 C5 C4 Cl1 116.58(11) . . ?
 C5 C4 C3 124.23(13) . . ?
 C5 C4 Br1 116.58(11) . . ?
 C4 C5 C6 118.58(14) . . ?
 C7 C6 C5 119.64(14) . . ?
 C6 C7 C8 120.23(14) . . ?
 C7 C8 C3 122.36(14) . . ?
 C10 C9 C14 114.46(14) . . ?
 C10 C9 B 126.24(14) . . ?
 C14 C9 B 119.11(14) . . ?
 C9 C10 Cl2 120.89(12) . . ?
 C9 C10 C11 123.81(17) . . ?
 C11 C10 Cl2 115.25(14) . . ?
 C12 C11 C10 119.09(18) . . ?
 C11 C12 C13 119.83(17) . . ?
 C12 C13 C14 119.98(19) . . ?
 C13 C14 C9 122.80(18) . . ?
 O B N 100.71(10) . . ?
 O B C3 112.21(11) . . ?
 O B C9 109.56(11) . . ?
 C3 B N 104.68(11) . . ?
 C9 B N 115.21(11) . . ?
 C9 B C3 113.75(11) . . ?

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
 N H1N O 0.77(3) 2.18(3) 2.8898(17) 153(3) 3_466
 N H2N Cl2 0.83(2) 2.72(2) 3.4741(13) 153(2) 3_466

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'

#===END
