# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_amji173
_database_code_depnum_ccdc_archive 'CCDC 1038711'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;
_audit_creation_date             2014-12-10
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H6 Al Cl6 N2, Al Cl4'
_chemical_formula_sum            'C10 H6 Al2 Cl10 N2'
_chemical_formula_weight         562.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C5 H3 Al1 N1 Cl5'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   7.1166(5)
_cell_length_b                   11.5660(8)
_cell_length_c                   25.5436(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.390(5)
_cell_angle_gamma                90
_cell_volume                     2101.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1748
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.1430
_cell_measurement_theta_min      3.4580
_exptl_absorpt_coefficient_mu    1.407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            6536
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_min         3.191
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 8.0714
_diffrn_measured_fraction_theta_full 0.9920
_diffrn_measured_fraction_theta_max 0.8453
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -47.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7110 -178.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   42.00   85.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3360 -132.0000   56.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -26.00   79.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3360   19.0000  120.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0021763000
_diffrn_orient_matrix_UB_12      -0.0612914000
_diffrn_orient_matrix_UB_13      -0.0006297000
_diffrn_orient_matrix_UB_21      0.0006842000
_diffrn_orient_matrix_UB_22      -0.0013094000
_diffrn_orient_matrix_UB_23      0.0277740000
_diffrn_orient_matrix_UB_31      -0.0996517000
_diffrn_orient_matrix_UB_32      0.0013065000
_diffrn_orient_matrix_UB_33      -0.0005023000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2844
_reflns_number_total             4115
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.074
_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)+(0.0138P)²+4.4984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1120
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H7(0.027) H3(0.036) H2(0.028) H8(0.033) H9(0.028) H4(0.032)
 Fixed X: H7(0.4729) H3(0.6007) H2(0.8156) H8(0.5267) H9(0.8042) H4(0.5926)
 Fixed Y: H7(0.356) H3(0.5399) H2(0.6647) H8(0.1702) H9(0.0731) H4(0.3453)
 Fixed Z: H7(0.5137) H3(0.786) H2(0.7486) H8(0.4808) H9(0.5041) H4(0.7593)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl2 Cl 0.7969(2) 0.22168(13) 0.68637(5) 0.0259(3) Uani 1 1 d . . . . .
Cl5 Cl 1.16200(18) 0.49695(14) 0.56098(5) 0.0266(3) Uani 1 1 d . . . . .
Cl3 Cl 0.67846(18) 0.49683(13) 0.58168(5) 0.0251(3) Uani 1 1 d . . . . .
Al1 Al 1.0610(2) 0.38744(15) 0.61961(6) 0.0164(4) Uani 1 1 d . . . . .
Cl6 Cl 1.28796(18) 0.30715(13) 0.65985(5) 0.0270(4) Uani 1 1 d . . . . .
Cl1 Cl 1.0862(2) 0.63366(13) 0.67253(6) 0.0310(4) Uani 1 1 d . . . . .
Cl4 Cl 1.0978(2) 0.12651(14) 0.57403(6) 0.0337(4) Uani 1 1 d . . . . .
Cl7 Cl 0.5138(2) 0.72235(14) 0.64566(6) 0.0334(4) Uani 1 1 d . . . . .
Cl10 Cl 0.8323(2) 0.91869(15) 0.69938(6) 0.0371(4) Uani 1 1 d . . . . .
Cl9 Cl 0.5058(2) 1.00846(14) 0.60609(6) 0.0327(4) Uani 1 1 d . . . . .
Cl8 Cl 0.8643(2) 0.82591(16) 0.56758(6) 0.0386(4) Uani 1 1 d . . . . .
Al2 Al 0.6846(2) 0.86890(15) 0.62958(6) 0.0187(4) Uani 1 1 d . . . . .
N1 N 0.9124(5) 0.4363(4) 0.68051(15) 0.0143(10) Uani 1 1 d . . . . .
N2 N 0.8716(6) 0.3039(4) 0.57408(15) 0.0149(10) Uani 1 1 d . . . . .
C10 C 0.8984(7) 0.1981(5) 0.5539(2) 0.0192(12) Uani 1 1 d . . . . .
C1 C 0.9200(7) 0.5462(5) 0.6991(2) 0.0175(12) Uani 1 1 d . . . . .
C5 C 0.7929(7) 0.3646(5) 0.7048(2) 0.0182(12) Uani 1 1 d . . . . .
C6 C 0.7131(7) 0.3603(5) 0.5578(2) 0.0183(12) Uani 1 1 d . . . . .
C7 C 0.5830(7) 0.3142(5) 0.5237(2) 0.0224(13) Uani 1 1 d . . . . .
H7 H 0.4729 0.3560 0.5137 0.027 Uiso 1 1 calc R U . . .
C3 C 0.6824(8) 0.5129(6) 0.7598(2) 0.0296(15) Uani 1 1 d . . . . .
H3 H 0.6007 0.5399 0.7860 0.036 Uiso 1 1 calc R U . . .
C2 C 0.8073(7) 0.5865(5) 0.7375(2) 0.0232(13) Uani 1 1 d . . . . .
H2 H 0.8156 0.6647 0.7486 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6158(8) 0.2051(6) 0.5042(2) 0.0278(15) Uani 1 1 d . . . . .
H8 H 0.5267 0.1702 0.4808 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7772(7) 0.1469(5) 0.5184(2) 0.0231(13) Uani 1 1 d . . . . .
H9 H 0.8042 0.0731 0.5041 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6759(7) 0.3986(6) 0.7437(2) 0.0264(14) Uani 1 1 d . . . . .
H4 H 0.5926 0.3453 0.7593 0.032 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
Cl2 0.0332(9) 0.0201(8) 0.0246(8) 0.0014(7) 0.0027(6) -0.0068(7)
Cl5 0.0234(8) 0.0344(9) 0.0221(7) 0.0067(7) 0.0034(5) -0.0050(7)
Cl3 0.0235(8) 0.0243(8) 0.0270(8) -0.0031(7) -0.0071(6) 0.0081(6)
Al1 0.0138(8) 0.0204(9) 0.0148(8) 0.0000(7) -0.0011(6) -0.0001(7)
Cl6 0.0188(8) 0.0343(9) 0.0275(8) 0.0014(7) -0.0057(6) 0.0064(6)
Cl1 0.0378(9) 0.0232(8) 0.0327(8) -0.0030(7) 0.0115(6) -0.0114(7)
Cl4 0.0314(9) 0.0312(9) 0.0382(9) -0.0116(8) -0.0094(6) 0.0150(7)
Cl7 0.0287(9) 0.0243(8) 0.0477(10) -0.0071(8) 0.0089(7) -0.0071(7)
Cl10 0.0453(10) 0.0337(9) 0.0315(9) -0.0059(8) -0.0178(7) -0.0020(8)
Cl9 0.0337(9) 0.0339(9) 0.0303(8) 0.0039(7) -0.0003(6) 0.0139(7)
Cl8 0.0351(9) 0.0498(11) 0.0316(9) 0.0008(8) 0.0147(7) 0.0092(8)
Al2 0.0186(9) 0.0197(9) 0.0178(8) -0.0017(8) -0.0006(6) 0.0001(8)
N1 0.013(2) 0.019(3) 0.011(2) 0.004(2) -0.0025(16) -0.003(2)
N2 0.017(2) 0.019(3) 0.010(2) 0.0034(19) -0.0024(17) -0.0001(19)
C10 0.021(3) 0.017(3) 0.020(3) 0.003(2) 0.002(2) 0.000(2)
C1 0.021(3) 0.014(3) 0.018(3) 0.007(2) -0.003(2) -0.004(2)
C5 0.013(3) 0.019(3) 0.022(3) 0.002(3) -0.004(2) -0.004(2)
C6 0.015(3) 0.021(3) 0.020(3) -0.003(3) 0.002(2) 0.002(2)
C7 0.019(3) 0.027(3) 0.021(3) 0.003(3) -0.002(2) 0.004(3)
C3 0.027(3) 0.043(4) 0.019(3) -0.007(3) 0.008(2) 0.001(3)
C2 0.027(3) 0.022(3) 0.020(3) 0.000(3) 0.000(2) 0.004(3)
C8 0.025(3) 0.037(4) 0.020(3) -0.001(3) -0.007(2) -0.011(3)
C9 0.025(3) 0.024(3) 0.021(3) -0.009(3) 0.001(2) -0.003(3)
C4 0.020(3) 0.035(4) 0.024(3) 0.002(3) 0.003(2) -0.009(3)

_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
Cl2 C5 1.719(6) . ?
Cl5 Al1 2.101(2) . ?
Cl3 C6 1.713(6) . ?
Al1 Cl6 2.109(2) . ?
Al1 N1 1.984(4) . ?
Al1 N2 2.007(4) . ?
Cl1 C1 1.709(5) . ?
Cl4 C10 1.711(5) . ?
Cl7 Al2 2.131(2) . ?
Cl10 Al2 2.127(2) . ?
Cl9 Al2 2.133(2) . ?
Cl8 Al2 2.119(2) . ?
N1 C1 1.357(7) . ?
N1 C5 1.350(6) . ?
N2 C10 1.343(7) . ?
N2 C6 1.359(6) . ?
C10 C9 1.371(7) . ?
C1 C2 1.364(7) . ?
C5 C4 1.370(7) . ?
C6 C7 1.365(7) . ?
C7 C8 1.378(8) . ?
C3 C2 1.365(8) . ?
C3 C4 1.384(9) . ?
C8 C9 1.373(8) . ?

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
Cl5 Al1 Cl6 109.96(9) . . ?
N1 Al1 Cl5 125.81(16) . . ?
N1 Al1 Cl6 99.18(13) . . ?
N1 Al1 N2 103.20(18) . . ?
N2 Al1 Cl5 96.54(14) . . ?
N2 Al1 Cl6 124.49(15) . . ?
Cl7 Al2 Cl9 108.48(9) . . ?
Cl10 Al2 Cl7 109.05(9) . . ?
Cl10 Al2 Cl9 108.08(10) . . ?
Cl8 Al2 Cl7 108.35(10) . . ?
Cl8 Al2 Cl10 113.27(9) . . ?
Cl8 Al2 Cl9 109.52(9) . . ?
C1 N1 Al1 121.5(4) . . ?
C5 N1 Al1 122.6(4) . . ?
C5 N1 C1 115.8(4) . . ?
C10 N2 Al1 124.1(3) . . ?
C10 N2 C6 116.4(4) . . ?
C6 N2 Al1 119.1(4) . . ?
N2 C10 Cl4 116.8(4) . . ?
N2 C10 C9 123.6(5) . . ?
C9 C10 Cl4 119.6(4) . . ?
N1 C1 Cl1 116.0(4) . . ?
N1 C1 C2 123.5(5) . . ?
C2 C1 Cl1 120.5(4) . . ?
N1 C5 Cl2 116.7(4) . . ?
N1 C5 C4 123.9(5) . . ?
C4 C5 Cl2 119.3(5) . . ?
N2 C6 Cl3 117.3(4) . . ?
N2 C6 C7 123.6(5) . . ?
C7 C6 Cl3 119.1(4) . . ?
C6 C7 C8 118.1(5) . . ?
C2 C3 C4 119.3(5) . . ?
C1 C2 C3 119.2(6) . . ?
C9 C8 C7 120.0(5) . . ?
C10 C9 C8 118.2(5) . . ?
C5 C4 C3 118.2(6) . . ?

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
Cl2 C5 C4 C3 176.7(4) . . . . ?
Cl3 C6 C7 C8 178.7(4) . . . . ?
Al1 N1 C1 Cl1 -8.1(5) . . . . ?
Al1 N1 C1 C2 173.5(4) . . . . ?
Al1 N1 C5 Cl2 8.4(5) . . . . ?
Al1 N1 C5 C4 -173.7(4) . . . . ?
Al1 N2 C10 Cl4 6.5(6) . . . . ?
Al1 N2 C10 C9 -172.7(4) . . . . ?
Al1 N2 C6 Cl3 -4.8(5) . . . . ?
Al1 N2 C6 C7 174.9(4) . . . . ?
Cl1 C1 C2 C3 -176.7(4) . . . . ?
Cl4 C10 C9 C8 178.2(4) . . . . ?
N1 C1 C2 C3 1.6(8) . . . . ?
N1 C5 C4 C3 -1.1(8) . . . . ?
N2 C10 C9 C8 -2.6(8) . . . . ?
N2 C6 C7 C8 -1.0(8) . . . . ?
C10 N2 C6 Cl3 -178.5(4) . . . . ?
C10 N2 C6 C7 1.3(8) . . . . ?
C1 N1 C5 Cl2 -174.0(4) . . . . ?
C1 N1 C5 C4 3.9(7) . . . . ?
C5 N1 C1 Cl1 174.2(3) . . . . ?
C5 N1 C1 C2 -4.1(7) . . . . ?
C6 N2 C10 Cl4 179.8(4) . . . . ?
C6 N2 C10 C9 0.6(8) . . . . ?
C6 C7 C8 C9 -1.1(8) . . . . ?
C7 C8 C9 C10 2.8(8) . . . . ?
C2 C3 C4 C5 -1.7(8) . . . . ?
C4 C3 C2 C1 1.5(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_amji116
_database_code_depnum_ccdc_archive 'CCDC 1038712'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;
_audit_creation_date             2014-12-10
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_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_melting_point          ?
_chemical_oxdiff_formula         C5H3Al1B1Cl8N1
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   7.2646(4)
_cell_length_b                   13.5445(8)
_cell_length_c                   14.7907(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.625(5)
_cell_angle_gamma                90
_cell_volume                     1442.46(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3045
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.4580
_cell_measurement_theta_min      3.6280
_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_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1839  -55.0000  152.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1839   37.0000   30.0000 102

#__ type_ start__ end____ width___ exp.time_
  3 omega  -19.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1839  -99.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
  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_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2274
_reflns_number_total             2607
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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       
;
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
;
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.055
_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
_refine_special_details          
;
 ?
;
_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)
;
_atom_sites_solution_hydrogens   geom
_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
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)

_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
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) . ?

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
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) . . ?

_olex2_date_sample_data_collection 1387270310.0
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_amji235a
_database_code_depnum_ccdc_archive 'CCDC 1038713'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;
_audit_creation_date             2014-12-10
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 2-(4-bromo-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
;
_chemical_formula_moiety         'C12 H15 B Br F O2'
_chemical_formula_sum            'C12 H15 B Br F O2'
_chemical_formula_weight         300.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H15B1Br1F1O2
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   13.8821(8)
_cell_length_b                   7.6711(4)
_cell_length_c                   12.4528(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.002(5)
_cell_angle_gamma                90
_cell_volume                     1325.30(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1769
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.9800
_cell_measurement_theta_min      4.2030
_exptl_absorpt_coefficient_mu    3.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56386
_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    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5945
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.865
_diffrn_reflns_theta_min         3.424
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.8698
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    4.00   80.00   1.0000    1.1050
omega____ theta____ kappa____ phi______ frames
    -       19.4509   57.0000  -60.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega   53.00   80.00   1.0000    1.1050
omega____ theta____ kappa____ phi______ frames
    -       19.4509  178.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   86.00   1.0000    1.1050
omega____ theta____ kappa____ phi______ frames
    -       19.4509   19.0000  -90.0000 106

#__ type_ start__ end____ width___ exp.time_
  4 omega  -95.00  -69.00   1.0000    1.1050
omega____ theta____ kappa____ phi______ frames
    -      -18.3571  178.0000  120.0000 26
;
_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      0.0225609000
_diffrn_orient_matrix_UB_12      -0.0472052000
_diffrn_orient_matrix_UB_13      0.0429344000
_diffrn_orient_matrix_UB_21      0.0456486000
_diffrn_orient_matrix_UB_22      0.0158832000
_diffrn_orient_matrix_UB_23      -0.0218961000
_diffrn_orient_matrix_UB_31      0.0043379000
_diffrn_orient_matrix_UB_32      0.0779031000
_diffrn_orient_matrix_UB_33      0.0304675000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2315
_reflns_number_total             3024
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
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
;
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      1.028
_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)+(0.0395P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1105
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H6(0.023) H9A(0.048) H9B(0.048) H9C(0.048) H5(0.029) H3(0.025)
 H12A(0.047) H12B(0.047) H12C(0.047) H8A(0.045) H8B(0.045) H8C(0.045)
 H11A(0.053) H11B(0.053) H11C(0.053)
 Fixed X: H6(0.917) H9A(0.5026) H9B(0.5289) H9C(0.5999) H5(1.0181) H3(0.8078)
 H12A(0.6935) H12B(0.6571) H12C(0.7701) H8A(0.5734) H8B(0.5238) H8C(0.4831)
 H11A(0.8042) H11B(0.695) H11C(0.74)
 Fixed Y: H6(0.0953) H9A(0.0094) H9B(-0.1229) H9C(0.0353) H5(0.2963)
 H3(0.4033) H12A(-0.164) H12B(-0.3598) H12C(-0.318) H8A(-0.356) H8B(-0.3855)
 H8C(-0.2393) H11A(-0.4371) H11B(-0.503) H11C(-0.3845)
 Fixed Z: H6(0.4413) H9A(0.3578) H9B(0.2639) H9C(0.2943) H5(0.5285) H3(0.7369)
 H12A(0.2042) H12B(0.2208) H12C(0.2227) H8A(0.5127) H8B(0.3961) H8C(0.4742)
 H11A(0.4009) H11B(0.4053) H11C(0.5001)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br 1.00175(3) 0.52837(6) 0.71506(3) 0.03180(16) Uani 1 1 d . . . . .
F1 F 0.68124(13) 0.2002(3) 0.65960(16) 0.0306(5) Uani 1 1 d . . . . .
O1 O 0.64373(16) -0.0507(3) 0.49192(18) 0.0206(6) Uani 1 1 d . . . . .
O2 O 0.77448(15) -0.1064(3) 0.39038(18) 0.0210(6) Uani 1 1 d . . . . .
B1 B 0.7373(3) -0.0119(5) 0.4727(3) 0.0182(9) Uani 1 1 d . . . . .
C4 C 0.9209(2) 0.3667(4) 0.6397(3) 0.0171(7) Uani 1 1 d . . . . .
C6 C 0.8942(2) 0.1577(5) 0.5012(3) 0.0193(8) Uani 1 1 d . . . . .
H6 H 0.9170 0.0953 0.4413 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5553(3) -0.0508(5) 0.3229(3) 0.0319(10) Uani 1 1 d . . . . .
H9A H 0.5026 0.0094 0.3578 0.048 Uiso 1 1 calc R U . . .
H9B H 0.5289 -0.1229 0.2639 0.048 Uiso 1 1 calc R U . . .
H9C H 0.5999 0.0353 0.2943 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6090(2) -0.1662(5) 0.4044(3) 0.0203(8) Uani 1 1 d . . . . .
C5 C 0.9548(3) 0.2768(5) 0.5525(3) 0.0241(9) Uani 1 1 d . . . . .
H5 H 1.0181 0.2963 0.5285 0.029 Uiso 1 1 calc R U . . .
C2 C 0.7722(2) 0.2220(5) 0.6219(3) 0.0181(8) Uani 1 1 d . . . . .
C3 C 0.8300(2) 0.3415(5) 0.6765(3) 0.0207(8) Uani 1 1 d . . . . .
H3 H 0.8078 0.4033 0.7369 0.025 Uiso 1 1 calc R U . . .
C1 C 0.8004(2) 0.1255(5) 0.5344(3) 0.0169(8) Uani 1 1 d . . . . .
C10 C 0.7054(3) -0.2439(5) 0.3630(3) 0.0221(8) Uani 1 1 d . . . . .
C12 C 0.7066(3) -0.2741(5) 0.2418(3) 0.0316(10) Uani 1 1 d . . . . .
H12A H 0.6935 -0.1640 0.2042 0.047 Uiso 1 1 calc R U . . .
H12B H 0.6571 -0.3598 0.2208 0.047 Uiso 1 1 calc R U . . .
H12C H 0.7701 -0.3180 0.2227 0.047 Uiso 1 1 calc R U . . .
C8 C 0.5414(3) -0.2984(5) 0.4509(3) 0.0302(9) Uani 1 1 d . . . . .
H8A H 0.5734 -0.3560 0.5127 0.045 Uiso 1 1 calc R U . . .
H8B H 0.5238 -0.3855 0.3961 0.045 Uiso 1 1 calc R U . . .
H8C H 0.4831 -0.2393 0.4742 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7391(3) -0.4065(5) 0.4226(3) 0.0355(10) Uani 1 1 d . . . . .
H11A H 0.8042 -0.4371 0.4009 0.053 Uiso 1 1 calc R U . . .
H11B H 0.6950 -0.5030 0.4053 0.053 Uiso 1 1 calc R U . . .
H11C H 0.7400 -0.3845 0.5001 0.053 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
Br1 0.0383(3) 0.0301(3) 0.0267(2) -0.00666(18) -0.00394(17) -0.0144(2)
F1 0.0161(10) 0.0407(15) 0.0352(12) -0.0095(11) 0.0039(9) -0.0050(10)
O1 0.0176(12) 0.0240(15) 0.0200(13) -0.0045(11) -0.0013(10) -0.0027(11)
O2 0.0199(12) 0.0228(14) 0.0204(13) -0.0082(11) 0.0022(10) -0.0069(12)
B1 0.019(2) 0.019(2) 0.0158(19) 0.0029(18) -0.0013(15) 0.0018(18)
C4 0.0210(17) 0.0126(18) 0.0170(17) 0.0016(15) -0.0075(14) -0.0022(16)
C6 0.0221(18) 0.020(2) 0.0155(16) -0.0023(15) -0.0016(14) -0.0020(17)
C9 0.028(2) 0.034(3) 0.032(2) 0.0022(19) -0.0116(17) 0.001(2)
C7 0.0221(18) 0.020(2) 0.0180(17) -0.0011(16) -0.0059(14) -0.0044(17)
C5 0.0221(19) 0.029(2) 0.0212(18) 0.0021(17) -0.0018(15) -0.0056(18)
C2 0.0117(16) 0.021(2) 0.0220(17) 0.0023(16) 0.0002(13) 0.0021(15)
C3 0.0225(18) 0.019(2) 0.0198(18) -0.0015(16) -0.0047(14) 0.0027(17)
C1 0.0174(17) 0.0166(19) 0.0163(17) 0.0014(15) -0.0027(13) -0.0012(16)
C10 0.0235(19) 0.022(2) 0.0209(18) -0.0052(17) -0.0024(14) -0.0064(17)
C12 0.033(2) 0.039(3) 0.0229(19) -0.0084(19) 0.0023(16) -0.014(2)
C8 0.027(2) 0.034(2) 0.030(2) -0.0050(19) 0.0017(16) -0.0089(19)
C11 0.040(2) 0.026(2) 0.041(2) 0.000(2) -0.0015(19) 0.006(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
Br1 C4 1.899(3) . ?
F1 C2 1.373(4) . ?
O1 B1 1.362(4) . ?
O1 C7 1.473(4) . ?
O2 B1 1.371(5) . ?
O2 C10 1.458(4) . ?
B1 C1 1.556(5) . ?
C4 C5 1.383(5) . ?
C4 C3 1.371(5) . ?
C6 C5 1.383(5) . ?
C6 C1 1.402(4) . ?
C9 C7 1.522(5) . ?
C7 C10 1.568(5) . ?
C7 C8 1.511(5) . ?
C2 C3 1.382(5) . ?
C2 C1 1.385(5) . ?
C10 C12 1.527(4) . ?
C10 C11 1.518(5) . ?

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
B1 O1 C7 106.9(3) . . ?
B1 O2 C10 107.2(3) . . ?
O1 B1 O2 113.7(3) . . ?
O1 B1 C1 125.8(3) . . ?
O2 B1 C1 120.5(3) . . ?
C5 C4 Br1 120.1(3) . . ?
C3 C4 Br1 117.5(3) . . ?
C3 C4 C5 122.3(3) . . ?
C5 C6 C1 122.5(3) . . ?
O1 C7 C9 106.5(3) . . ?
O1 C7 C10 102.2(2) . . ?
O1 C7 C8 108.1(3) . . ?
C9 C7 C10 113.9(3) . . ?
C8 C7 C9 110.5(3) . . ?
C8 C7 C10 114.8(3) . . ?
C4 C5 C6 118.3(3) . . ?
F1 C2 C3 116.0(3) . . ?
F1 C2 C1 119.5(3) . . ?
C3 C2 C1 124.5(3) . . ?
C4 C3 C2 117.0(3) . . ?
C6 C1 B1 119.1(3) . . ?
C2 C1 B1 125.5(3) . . ?
C2 C1 C6 115.4(3) . . ?
O2 C10 C7 102.1(3) . . ?
O2 C10 C12 108.1(3) . . ?
O2 C10 C11 106.9(3) . . ?
C12 C10 C7 115.0(3) . . ?
C11 C10 C7 113.8(3) . . ?
C11 C10 C12 110.2(3) . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_amji207
_database_code_depnum_ccdc_archive 'CCDC 1038714'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;
_audit_creation_date             2014-12-10
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
2-(4-chloro-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
;
_chemical_formula_moiety         'C12 H15 B Cl F O2'
_chemical_formula_sum            'C12 H15 B Cl F O2'
_chemical_formula_weight         256.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H15B1Cl1F1O2
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   13.8661(7)
_cell_length_b                   7.5020(4)
_cell_length_c                   12.4291(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.422(5)
_cell_angle_gamma                90
_cell_volume                     1291.77(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1463
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.7100
_cell_measurement_theta_min      3.5370
_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_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -94.00   10.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      -20.4767  -37.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   55.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      -20.4767   19.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
  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_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2005
_reflns_number_total             2898
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
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
;
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.033
_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
_refine_special_details          
;
 ?
;
_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)
;
_atom_sites_solution_hydrogens   geom
_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
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)

_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 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) . ?

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
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) . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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
