#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:47:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180276 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/62/7116288.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_7116288
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         'C5 H3 B Cl4 N, Al Cl4'
_chemical_formula_sum            'C5 H3 Al B Cl8 N'
_chemical_formula_weight         398.47
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
_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                 97.625(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2646(4)
_cell_length_b                   13.5445(8)
_cell_length_c                   14.7907(7)
_cell_measurement_reflns_used    3045
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.4580
_cell_measurement_theta_min      3.6280
_cell_volume                     1442.47(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      150.0
_diffrn_detector_area_resol_mean 8.0714
_diffrn_measured_fraction_theta_full 0.9926
_diffrn_measured_fraction_theta_max 0.8396
_diffrn_measurement_details
;
  1 omega  -30.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1839  -55.0000  152.0000 36

  2 omega  -50.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1839   37.0000   30.0000 102

  3 omega  -19.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1839  -99.0000    0.0000 43

  4 omega    0.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6526   57.0000 -150.0000 53
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0691069000
_diffrn_orient_matrix_UB_12      -0.0313639000
_diffrn_orient_matrix_UB_13      0.0229792000
_diffrn_orient_matrix_UB_21      0.0446561000
_diffrn_orient_matrix_UB_22      0.0415158000
_diffrn_orient_matrix_UB_23      0.0224798000
_diffrn_orient_matrix_UB_31      -0.0540979000
_diffrn_orient_matrix_UB_32      -0.0058516000
_diffrn_orient_matrix_UB_33      0.0361988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5221
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_min         2.982
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_description       irregular
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0376
_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)+(0.0399P)²+0.6699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2274
_reflns_number_total             2607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4cc10153g2.cif
_cod_data_source_block           amji116
_cod_depositor_comments
'Adding full bibliography for 7116287--7116290.cif.'
_cod_original_cell_volume        1442.46(13)
_cod_database_code               7116288
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         C5H3Al1B1Cl8N1
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.032) H4(0.031) H3(0.032)
 Fixed X: H2(0.8143) H4(0.498) H3(0.5342)
 Fixed Y: H2(0.0522) H4(0.2821) H3(0.1394)
 Fixed Z: H2(0.3349) H4(0.3965) H3(0.3124)
;
_olex2_date_sample_data_collection 1387270310.0
_olex2_submission_special_instructions 'No special instructions were received'
_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+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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl5 Cl 0.93901(11) 0.58415(6) 0.89854(5) 0.0297(2) Uani 1 1 d . .
Cl2 Cl 0.73790(11) 0.37518(6) 0.53896(6) 0.0343(2) Uani 1 1 d . .
Cl1 Cl 1.14729(11) 0.08649(6) 0.45425(6) 0.0319(2) Uani 1 1 d . .
Cl7 Cl 1.09246(11) 0.54873(7) 0.68653(5) 0.0353(2) Uani 1 1 d . .
Cl8 Cl 0.84382(12) 0.76059(6) 0.73057(6) 0.0334(2) Uani 1 1 d . .
Al1 Al 0.87368(12) 0.60614(7) 0.75444(6) 0.0205(2) Uani 1 1 d . .
Cl6 Cl 0.62271(11) 0.53199(6) 0.70270(6) 0.0314(2) Uani 1 1 d . .
Cl3 Cl 1.08959(12) 0.20364(8) 0.65905(5) 0.0426(3) Uani 1 1 d . .
C2 C 0.7981(4) 0.1100(2) 0.3693(2) 0.0269(7) Uani 1 1 d . .
H2 H 0.8143 0.0522 0.3349 0.032 Uiso 1 1 calc R U
Cl4 Cl 1.22283(12) 0.34777(7) 0.52709(7) 0.0427(3) Uani 1 1 d . .
C4 C 0.6107(4) 0.2457(2) 0.4062(2) 0.0257(7) Uani 1 1 d . .
H4 H 0.4980 0.2821 0.3965 0.031 Uiso 1 1 calc R U
N1 N 0.9167(3) 0.22579(18) 0.48305(16) 0.0204(6) Uani 1 1 d . .
C1 C 0.9377(4) 0.1437(2) 0.4327(2) 0.0230(7) Uani 1 1 d . .
C5 C 0.7529(4) 0.2759(2) 0.47000(19) 0.0223(7) Uani 1 1 d . .
C3 C 0.6330(4) 0.1617(2) 0.3561(2) 0.0268(7) Uani 1 1 d . .
H3 H 0.5342 0.1394 0.3124 0.032 Uiso 1 1 calc R U
B1 B 1.0741(5) 0.2591(3) 0.5550(3) 0.0299(9) Uani 1 1 d . .
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
Cl5 0.0319(4) 0.0355(5) 0.0208(4) 0.0060(4) 0.0001(3) -0.0038(4)
Cl2 0.0378(5) 0.0296(5) 0.0357(5) -0.0099(4) 0.0061(4) 0.0046(4)
Cl1 0.0271(4) 0.0288(5) 0.0398(5) 0.0063(4) 0.0042(3) 0.0108(3)
Cl7 0.0299(4) 0.0463(6) 0.0309(4) 0.0023(4) 0.0079(3) 0.0095(4)
Cl8 0.0382(5) 0.0194(4) 0.0417(5) 0.0079(4) 0.0024(4) -0.0025(3)
Al1 0.0206(5) 0.0194(5) 0.0209(5) 0.0030(4) -0.0001(4) 0.0002(4)
Cl6 0.0272(4) 0.0272(4) 0.0381(5) -0.0049(4) -0.0014(3) -0.0042(3)
Cl3 0.0423(5) 0.0591(6) 0.0251(4) 0.0040(5) -0.0002(4) 0.0038(5)
C2 0.0348(18) 0.0202(17) 0.0259(16) -0.0006(15) 0.0051(14) -0.0026(14)
Cl4 0.0362(5) 0.0417(6) 0.0502(6) -0.0070(5) 0.0062(4) -0.0119(4)
C4 0.0231(16) 0.0270(18) 0.0258(16) 0.0054(15) -0.0013(13) 0.0051(14)
N1 0.0207(13) 0.0209(14) 0.0194(12) 0.0034(12) 0.0025(10) -0.0024(11)
C1 0.0231(15) 0.0204(16) 0.0257(16) 0.0075(14) 0.0040(13) 0.0031(13)
C5 0.0266(16) 0.0206(16) 0.0208(15) 0.0035(14) 0.0071(13) 0.0021(14)
C3 0.0297(17) 0.0247(17) 0.0238(16) 0.0045(15) -0.0044(13) -0.0045(14)
B1 0.0268(19) 0.031(2) 0.031(2) -0.0056(18) 0.0003(16) 0.0052(17)
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'
Al Al 0.0645 0.0514 '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'
N N 0.0061 0.0033 '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
Cl7 Al1 Cl5 109.68(5)
Cl8 Al1 Cl5 107.83(5)
Cl8 Al1 Cl7 110.22(5)
Cl8 Al1 Cl6 109.87(5)
Cl6 Al1 Cl5 110.95(5)
Cl6 Al1 Cl7 108.29(5)
C1 C2 C3 118.6(3)
C5 C4 C3 119.1(3)
C1 N1 C5 119.4(3)
C1 N1 B1 119.8(3)
C5 N1 B1 120.8(3)
C2 C1 Cl1 122.7(3)
N1 C1 Cl1 115.7(2)
N1 C1 C2 121.5(3)
C4 C5 Cl2 123.2(2)
N1 C5 Cl2 115.7(2)
N1 C5 C4 121.0(3)
C4 C3 C2 120.3(3)
Cl3 B1 Cl4 124.2(2)
N1 B1 Cl3 117.0(3)
N1 B1 Cl4 118.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl5 Al1 2.1420(11)
Cl2 C5 1.700(3)
Cl1 C1 1.701(3)
Cl7 Al1 2.1362(12)
Cl8 Al1 2.1278(12)
Al1 Cl6 2.1327(12)
Cl3 B1 1.702(4)
C2 C1 1.366(4)
C2 C3 1.381(4)
Cl4 B1 1.703(4)
C4 C5 1.366(4)
C4 C3 1.379(4)
N1 C1 1.358(4)
N1 C5 1.361(4)
N1 B1 1.524(4)
