# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1406327'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013

_chemical_name_systematic        
Pyridino[4,3-c]-1,3-dihydro-1-hydroxy-3-mezytyl[2,1]oxaborole
_chemical_name_common            ?
_chemical_melting_point          203
_chemical_formula_moiety         'C15 H16 B N O2'
_chemical_formula_sum            'C15 H16 B N O2'
_chemical_formula_weight         253.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.9283(4)
_cell_length_b                   10.0001(2)
_cell_length_c                   20.1811(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2609.10(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5528
_cell_measurement_theta_min      4.3810
_cell_measurement_theta_max      61.8520

_exptl_crystal_description       unspecified
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_min  0.88191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195
_diffrn_reflns_number            13550
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.382
_diffrn_reflns_theta_max         62.280
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.872
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.872
_reflns_number_total             2055
_reflns_number_gt                1750
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1176P)²+4.2676P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2055
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   0.754
_refine_ls_restrained_S_all      0.754
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C16 C 0.76555(17) 0.2837(2) 0.61654(11) 0.0271(5) Uani 1 1 d . . . . .
H16 H 0.7771 0.2465 0.6592 0.032 Uiso 1 1 calc R U . . .
C1 C 0.9759(2) 0.4688(2) 0.29748(12) 0.0356(6) Uani 1 1 d . . . . .
C2 C 1.02369(18) 0.4437(2) 0.35777(12) 0.0330(6) Uani 1 1 d . . . . .
H2A H 1.0885 0.4850 0.3665 0.040 Uiso 1 1 calc R U . . .
C3 C 0.98106(17) 0.3610(2) 0.40591(11) 0.0277(5) Uani 1 1 d . . . . .
C4 C 0.88597(17) 0.2977(2) 0.39198(11) 0.0258(5) Uani 1 1 d . . . . .
C5 C 0.83442(18) 0.3242(2) 0.33214(11) 0.0288(5) Uani 1 1 d . . . . .
C6 C 0.88060(19) 0.4091(2) 0.28636(12) 0.0335(6) Uani 1 1 d . . . . .
H6 H 0.8456 0.4270 0.2459 0.040 Uiso 1 1 calc R U . . .
C7 C 1.03645(18) 0.3444(2) 0.47073(12) 0.0327(6) Uani 1 1 d . . . . .
H7A H 1.0977 0.4021 0.4715 0.049 Uiso 1 1 calc R U . . .
H7B H 1.0577 0.2509 0.4759 0.049 Uiso 1 1 calc R U . . .
H7C H 0.9901 0.3692 0.5071 0.049 Uiso 1 1 calc R U . . .
C8 C 0.72914(19) 0.2659(3) 0.31631(12) 0.0355(6) Uani 1 1 d . . . . .
H8A H 0.6812 0.2855 0.3526 0.053 Uiso 1 1 calc R U . . .
H8B H 0.7352 0.1688 0.3108 0.053 Uiso 1 1 calc R U . . .
H8C H 0.7029 0.3055 0.2752 0.053 Uiso 1 1 calc R U . . .
C9 C 1.0241(2) 0.5602(3) 0.24644(14) 0.0471(7) Uani 1 1 d . . . . .
H9A H 0.9794 0.5645 0.2073 0.071 Uiso 1 1 calc R U . . .
H9B H 1.0921 0.5253 0.2337 0.071 Uiso 1 1 calc R U . . .
H9C H 1.0321 0.6499 0.2652 0.071 Uiso 1 1 calc R U . . .
C10 C 0.83437(17) 0.2085(2) 0.44276(11) 0.0254(5) Uani 1 1 d . . . . .
H10 H 0.7776 0.1582 0.4201 0.030 Uiso 1 1 calc R U . . .
C12 C 0.70639(18) 0.3979(2) 0.60954(11) 0.0275(5) Uani 1 1 d . . . . .
H12 H 0.6764 0.4368 0.6480 0.033 Uiso 1 1 calc R U . . .
C13 C 0.73023(17) 0.4003(2) 0.49579(11) 0.0254(5) Uani 1 1 d . . . . .
H13 H 0.7194 0.4409 0.4538 0.030 Uiso 1 1 calc R U . . .
C14 C 0.78742(16) 0.2844(2) 0.50029(11) 0.0240(5) Uani 1 1 d . . . . .
C15 C 0.80797(16) 0.2236(2) 0.56083(11) 0.0244(5) Uani 1 1 d . . . . .
B1 B 0.8819(2) 0.0960(2) 0.54492(13) 0.0256(6) Uani 1 1 d . . . . .
N1 N 0.68962(13) 0.45638(16) 0.55042(9) 0.0242(4) Uani 1 1 d . . . . .
O1 O 0.90184(11) 0.11295(14) 0.47337(7) 0.0255(4) Uani 1 1 d . . . . .
O2 O 0.96824(12) 0.07943(14) 0.58623(8) 0.0285(4) Uani 1 1 d . . . . .
H2 H 1.0015 0.0114 0.5743 0.043 Uiso 1 1 calc R U . . .


_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
C16 C12 1.382(3) . ?
C16 C15 1.388(3) . ?
C16 H16 0.9500 . ?
C1 C6 1.387(4) . ?
C1 C2 1.388(4) . ?
C1 C9 1.511(3) . ?
C2 C3 1.390(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.411(3) . ?
C3 C7 1.501(3) . ?
C4 C5 1.405(3) . ?
C4 C10 1.514(3) . ?
C5 C6 1.390(3) . ?
C5 C8 1.515(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O1 1.433(3) . ?
C10 C14 1.515(3) . ?
C10 H10 1.0000 . ?
C12 N1 1.346(3) . ?
C12 H12 0.9500 . ?
C13 N1 1.344(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C15 B1 1.627(3) . ?
B1 O2 1.402(3) . ?
B1 O1 1.476(3) . ?
B1 N1 1.679(3) 8_755 ?
N1 B1 1.679(3) 8_765 ?
O2 H2 0.8400 . ?

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
C12 C16 C15 119.6(2) . . ?
C12 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C6 C1 C2 117.4(2) . . ?
C6 C1 C9 121.1(2) . . ?
C2 C1 C9 121.6(2) . . ?
C1 C2 C3 123.0(2) . . ?
C1 C2 H2A 118.5 . . ?
C3 C2 H2A 118.5 . . ?
C2 C3 C4 118.2(2) . . ?
C2 C3 C7 119.1(2) . . ?
C4 C3 C7 122.6(2) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 C10 118.95(19) . . ?
C3 C4 C10 120.9(2) . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 C8 118.8(2) . . ?
C4 C5 C8 122.4(2) . . ?
C1 C6 C5 122.5(2) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C14 104.35(17) . . ?
O1 C10 C4 114.62(17) . . ?
C14 C10 C4 113.55(17) . . ?
O1 C10 H10 108.0 . . ?
C14 C10 H10 108.0 . . ?
C4 C10 H10 108.0 . . ?
N1 C12 C16 122.6(2) . . ?
N1 C12 H12 118.7 . . ?
C16 C12 H12 118.7 . . ?
N1 C13 C14 120.4(2) . . ?
N1 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 121.9(2) . . ?
C13 C14 C10 125.93(19) . . ?
C15 C14 C10 112.18(18) . . ?
C14 C15 C16 116.56(19) . . ?
C14 C15 B1 106.39(18) . . ?
C16 C15 B1 137.0(2) . . ?
O2 B1 O1 117.1(2) . . ?
O2 B1 C15 116.30(19) . . ?
O1 B1 C15 101.85(17) . . ?
O2 B1 N1 107.51(17) . 8_755 ?
O1 B1 N1 104.84(17) . 8_755 ?
C15 B1 N1 108.40(17) . 8_755 ?
C13 N1 C12 118.91(18) . . ?
C13 N1 B1 120.53(17) . 8_765 ?
C12 N1 B1 120.56(17) . 8_765 ?
C10 O1 B1 113.08(16) . . ?
B1 O2 H2 109.5 . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 1406328'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013

_chemical_name_systematic        
2-Fluoropyridino[4,3-c]-1,3-dihydro-1-hydroxy-3-(2?-methoxyphenyl)[2,1]oxaborole
_chemical_name_common            ?
_chemical_melting_point          168
_chemical_formula_moiety         'C13 H11 B F N O3'
_chemical_formula_sum            'C13 H11 B F N O3'
_chemical_formula_weight         259.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   11.0022(3)
_cell_length_b                   7.9623(2)
_cell_length_c                   15.0557(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.381(3)
_cell_angle_gamma                90
_cell_volume                     1236.35(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    4666
_cell_measurement_theta_min      4.3150
_cell_measurement_theta_max      76.2210
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_min  0.87246
_exptl_absorpt_correction_T_max  1.00000
_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.
;

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      air
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4391
_diffrn_reflns_number            8856
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.340
_diffrn_reflns_theta_max         76.675
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2568
_reflns_number_gt                2282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.4070P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2568
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
B1 B 0.68501(13) -0.28894(19) 0.32993(10) 0.0245(3) Uani 1 1 d . . . . .
F1 F 0.43467(8) 0.09969(10) 0.10755(5) 0.0325(2) Uani 1 1 d . . . . .
O3 O 0.75057(9) -0.42278(12) 0.37590(6) 0.0280(2) Uani 1 1 d . . . . .
O1 O 0.69984(8) -0.12871(12) 0.36695(6) 0.0252(2) Uani 1 1 d . . . . .
O2 O 0.41288(9) -0.15020(12) 0.34159(7) 0.0306(2) Uani 1 1 d . . . . .
N1 N 0.41650(10) -0.16552(15) 0.05252(7) 0.0275(3) Uani 1 1 d . . . . .
C3 C 0.58540(12) -0.28097(17) 0.22528(9) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.46799(12) -0.06312(18) 0.12412(9) 0.0254(3) Uani 1 1 d . . . . .
C6 C 0.53555(12) 0.09094(17) 0.34015(9) 0.0247(3) Uani 1 1 d . . . . .
C4 C 0.53180(12) -0.39326(18) 0.15047(9) 0.0273(3) Uani 1 1 d . . . . .
H4 H 0.5525 -0.5095 0.1575 0.033 Uiso 1 1 calc R U . . .
C11 C 0.56036(13) 0.26048(18) 0.35798(9) 0.0286(3) Uani 1 1 d . . . . .
H11 H 0.6294 0.3110 0.3435 0.034 Uiso 1 1 calc R U . . .
C13 C 0.62005(12) -0.00834(17) 0.29910(8) 0.0238(3) Uani 1 1 d . . . . .
H13 H 0.6790 0.0721 0.2830 0.029 Uiso 1 1 calc R U . . .
C7 C 0.43310(12) 0.01647(17) 0.36194(9) 0.0266(3) Uani 1 1 d . . . . .
C2 C 0.55201(12) -0.11261(17) 0.21213(9) 0.0241(3) Uani 1 1 d . . . . .
C8 C 0.36054(14) 0.11326(19) 0.40218(10) 0.0323(3) Uani 1 1 d . . . . .
H8 H 0.2925 0.0633 0.4182 0.039 Uiso 1 1 calc R U . . .
C9 C 0.38788(14) 0.2833(2) 0.41896(11) 0.0362(3) Uani 1 1 d . . . . .
H9 H 0.3378 0.3489 0.4463 0.043 Uiso 1 1 calc R U . . .
C5 C 0.44757(12) -0.32982(18) 0.06571(9) 0.0286(3) Uani 1 1 d . . . . .
H5 H 0.4100 -0.4053 0.0146 0.034 Uiso 1 1 calc R U . . .
C10 C 0.48661(14) 0.35839(19) 0.39655(10) 0.0347(3) Uani 1 1 d . . . . .
H10 H 0.5038 0.4750 0.4073 0.042 Uiso 1 1 calc R U . . .
C12 C 0.30151(14) -0.22625(19) 0.35396(11) 0.0354(3) Uani 1 1 d . . . . .
H12A H 0.2977 -0.3453 0.3368 0.053 Uiso 1 1 calc R U . . .
H12B H 0.2227 -0.1696 0.3132 0.053 Uiso 1 1 calc R U . . .
H12C H 0.3080 -0.2157 0.4203 0.053 Uiso 1 1 calc R U . . .
H3A H 0.806(2) -0.400(2) 0.4366(15) 0.053 Uiso 1 1 d . U . . .


_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
B1 O3 1.3369(18) . ?
B1 O1 1.3790(17) . ?
B1 C3 1.5763(18) . ?
F1 C1 1.3467(16) . ?
O3 H3A 0.92(2) . ?
O1 C13 1.4519(15) . ?
O2 C7 1.3627(17) . ?
O2 C12 1.4359(16) . ?
N1 C1 1.3124(17) . ?
N1 C5 1.3492(19) . ?
C3 C2 1.3858(19) . ?
C3 C4 1.3976(18) . ?
C1 C2 1.3829(17) . ?
C6 C11 1.3849(19) . ?
C6 C7 1.4097(18) . ?
C6 C13 1.5070(17) . ?
C4 C5 1.3851(18) . ?
C4 H4 0.9500 . ?
C11 C10 1.390(2) . ?
C11 H11 0.9500 . ?
C13 C2 1.5105(17) . ?
C13 H13 1.0000 . ?
C7 C8 1.3911(19) . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C5 H5 0.9500 . ?
C10 H10 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
O3 B1 O1 124.17(12) . . ?
O3 B1 C3 127.70(12) . . ?
O1 B1 C3 108.05(11) . . ?
B1 O3 H3A 113.9(12) . . ?
B1 O1 C13 111.65(10) . . ?
C7 O2 C12 117.48(11) . . ?
C1 N1 C5 117.82(11) . . ?
C2 C3 C4 119.16(12) . . ?
C2 C3 B1 103.84(11) . . ?
C4 C3 B1 136.98(12) . . ?
N1 C1 F1 115.73(11) . . ?
N1 C1 C2 124.28(13) . . ?
F1 C1 C2 119.99(12) . . ?
C11 C6 C7 118.98(12) . . ?
C11 C6 C13 118.86(12) . . ?
C7 C6 C13 122.16(12) . . ?
C5 C4 C3 117.92(13) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C6 C11 C10 121.57(13) . . ?
C6 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
O1 C13 C6 111.47(10) . . ?
O1 C13 C2 104.04(10) . . ?
C6 C13 C2 116.97(10) . . ?
O1 C13 H13 108.0 . . ?
C6 C13 H13 108.0 . . ?
C2 C13 H13 108.0 . . ?
O2 C7 C8 124.33(12) . . ?
O2 C7 C6 116.01(11) . . ?
C8 C7 C6 119.67(13) . . ?
C1 C2 C3 117.90(12) . . ?
C1 C2 C13 129.65(12) . . ?
C3 C2 C13 112.41(11) . . ?
C7 C8 C9 119.86(13) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 121.04(13) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
N1 C5 C4 122.90(12) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C9 C10 C11 118.87(14) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
