# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1852252'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 (R,E)-2-(((1-phenylethyl)imino)methyl)phenol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   18.196(19)
_cell_length_b                   5.857(6)
_cell_length_c                   14.535(16)
_cell_angle_alpha                90
_cell_angle_beta                 128.41(2)
_cell_angle_gamma                90
_cell_volume                     1214(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.239
_cell_measurement_theta_max      30.595

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   0.6919
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7834
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.239
_diffrn_reflns_theta_max         30.595
_diffrn_reflns_theta_full        25.243
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3586
_reflns_number_gt                3269
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.918
_reflns_Friedel_fraction_full    0.989

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.3374P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1366 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_chemical_absolute_configuration R
_refine_ls_number_reflns         3586
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0947
_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
O1 O 0.38214(9) 0.2680(2) 0.46298(12) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.45227(9) 0.6027(2) 0.61156(11) 0.0249(3) Uani 1 1 d . . . . .
C1 C 0.65433(11) 0.2532(3) 1.00843(14) 0.0308(4) Uani 1 1 d . . . . .
H1 H 0.6797 0.1489 1.0716 0.037 Uiso 1 1 calc R U . . .
C2 C 0.61249(12) 0.4537(4) 1.00542(14) 0.0322(4) Uani 1 1 d . . . . .
H4 H 0.6094 0.4874 1.0669 0.039 Uiso 1 1 calc R U . . .
C3 C 0.57483(11) 0.6066(3) 0.91224(13) 0.0270(3) Uani 1 1 d . . . . .
H5 H 0.5473 0.7450 0.9115 0.032 Uiso 1 1 calc R U . . .
C4 C 0.57737(10) 0.5577(3) 0.82033(13) 0.0222(3) Uani 1 1 d . . . . .
C5 C 0.53207(11) 0.7198(3) 0.71693(13) 0.0237(3) Uani 1 1 d . . . . .
H6 H 0.5088 0.8578 0.7324 0.028 Uiso 1 1 calc R U . . .
C6 C 0.37376(11) 0.7069(3) 0.54549(13) 0.0229(3) Uani 1 1 d . . . . .
H11 H 0.3671 0.8527 0.5683 0.027 Uiso 1 1 calc R U . . .
C7 C 0.29408(10) 0.6056(3) 0.43551(13) 0.0223(3) Uani 1 1 d . . . . .
C8 C 0.30252(11) 0.3908(3) 0.39756(14) 0.0253(3) Uani 1 1 d . . . . .
C9 C 0.22730(12) 0.3060(3) 0.28838(15) 0.0311(4) Uani 1 1 d . . . . .
H8 H 0.2326 0.1629 0.2622 0.037 Uiso 1 1 calc R U . . .
C10 C 0.14509(12) 0.4297(4) 0.21816(15) 0.0337(4) Uani 1 1 d . . . . .
H2 H 0.0946 0.3713 0.1433 0.040 Uiso 1 1 calc R U . . .
C11 C 0.65895(12) 0.2058(3) 0.91891(15) 0.0321(4) Uani 1 1 d . . . . .
H15 H 0.6889 0.0702 0.9217 0.038 Uiso 1 1 calc R U . . .
C12 C 0.61997(12) 0.3555(3) 0.82471(15) 0.0281(3) Uani 1 1 d . . . . .
H3 H 0.6224 0.3196 0.7629 0.034 Uiso 1 1 calc R U . . .
C13 C 0.20954(11) 0.7249(3) 0.36329(14) 0.0274(3) Uani 1 1 d . . . . .
H7 H 0.2032 0.8676 0.3888 0.033 Uiso 1 1 calc R U . . .
C14 C 0.13461(12) 0.6389(4) 0.25493(15) 0.0328(4) Uani 1 1 d . . . . .
H10 H 0.0772 0.7208 0.2067 0.039 Uiso 1 1 calc R U . . .
C15 C 0.59843(13) 0.7947(3) 0.69167(16) 0.0312(4) Uani 1 1 d . . . . .
H13 H 0.6179 0.6610 0.6711 0.047 Uiso 1 1 calc R U . . .
H12 H 0.6538 0.8680 0.7616 0.047 Uiso 1 1 calc R U . . .
H14 H 0.5661 0.9032 0.6262 0.047 Uiso 1 1 calc R U . . .
H9 H 0.4254(17) 0.352(5) 0.531(2) 0.047 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
O1 C8 1.345(2) . ?
O1 H9 0.93(3) . ?
N1 C6 1.277(2) . ?
N1 C5 1.470(2) . ?
C1 C11 1.383(3) . ?
C1 C2 1.385(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(3) . ?
C2 H4 0.9500 . ?
C3 C4 1.395(2) . ?
C3 H5 0.9500 . ?
C4 C12 1.395(3) . ?
C4 C5 1.517(2) . ?
C5 C15 1.529(3) . ?
C5 H6 1.0000 . ?
C6 C7 1.459(2) . ?
C6 H11 0.9500 . ?
C7 C13 1.396(2) . ?
C7 C8 1.420(3) . ?
C8 C9 1.393(2) . ?
C9 C10 1.381(3) . ?
C9 H8 0.9500 . ?
C10 C14 1.396(3) . ?
C10 H2 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H15 0.9500 . ?
C12 H3 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H7 0.9500 . ?
C14 H10 0.9500 . ?
C15 H13 0.9800 . ?
C15 H12 0.9800 . ?
C15 H14 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
C8 O1 H9 107.2(16) . . ?
C6 N1 C5 118.68(15) . . ?
C11 C1 C2 119.59(16) . . ?
C11 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.18(16) . . ?
C1 C2 H4 119.9 . . ?
C3 C2 H4 119.9 . . ?
C4 C3 C2 120.58(17) . . ?
C4 C3 H5 119.7 . . ?
C2 C3 H5 119.7 . . ?
C12 C4 C3 118.60(15) . . ?
C12 C4 C5 121.41(15) . . ?
C3 C4 C5 119.97(16) . . ?
N1 C5 C4 108.50(15) . . ?
N1 C5 C15 107.45(15) . . ?
C4 C5 C15 113.18(14) . . ?
N1 C5 H6 109.2 . . ?
C4 C5 H6 109.2 . . ?
C15 C5 H6 109.2 . . ?
N1 C6 C7 121.02(15) . . ?
N1 C6 H11 119.5 . . ?
C7 C6 H11 119.5 . . ?
C13 C7 C8 119.07(15) . . ?
C13 C7 C6 120.05(15) . . ?
C8 C7 C6 120.81(15) . . ?
O1 C8 C9 118.65(16) . . ?
O1 C8 C7 121.89(15) . . ?
C9 C8 C7 119.45(16) . . ?
C10 C9 C8 120.10(17) . . ?
C10 C9 H8 119.9 . . ?
C8 C9 H8 119.9 . . ?
C9 C10 C14 121.35(17) . . ?
C9 C10 H2 119.3 . . ?
C14 C10 H2 119.3 . . ?
C1 C11 C12 120.47(18) . . ?
C1 C11 H15 119.8 . . ?
C12 C11 H15 119.8 . . ?
C11 C12 C4 120.55(16) . . ?
C11 C12 H3 119.7 . . ?
C4 C12 H3 119.7 . . ?
C14 C13 C7 121.22(17) . . ?
C14 C13 H7 119.4 . . ?
C7 C13 H7 119.4 . . ?
C13 C14 C10 118.78(17) . . ?
C13 C14 H10 120.6 . . ?
C10 C14 H10 120.6 . . ?
C5 C15 H13 109.5 . . ?
C5 C15 H12 109.5 . . ?
H13 C15 H12 109.5 . . ?
C5 C15 H14 109.5 . . ?
H13 C15 H14 109.5 . . ?
H12 C15 H14 109.5 . . ?

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
C11 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C12 -1.3(2) . . . . ?
C2 C3 C4 C5 177.07(15) . . . . ?
C6 N1 C5 C4 132.07(15) . . . . ?
C6 N1 C5 C15 -105.23(17) . . . . ?
C12 C4 C5 N1 64.2(2) . . . . ?
C3 C4 C5 N1 -114.16(17) . . . . ?
C12 C4 C5 C15 -55.0(2) . . . . ?
C3 C4 C5 C15 126.68(16) . . . . ?
C5 N1 C6 C7 175.61(13) . . . . ?
N1 C6 C7 C13 -178.51(14) . . . . ?
N1 C6 C7 C8 -1.7(2) . . . . ?
C13 C7 C8 O1 179.84(15) . . . . ?
C6 C7 C8 O1 2.9(2) . . . . ?
C13 C7 C8 C9 1.4(2) . . . . ?
C6 C7 C8 C9 -175.50(15) . . . . ?
O1 C8 C9 C10 -178.90(15) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C14 -1.0(3) . . . . ?
C2 C1 C11 C12 -1.5(3) . . . . ?
C1 C11 C12 C4 1.3(3) . . . . ?
C3 C4 C12 C11 0.1(2) . . . . ?
C5 C4 C12 C11 -178.25(16) . . . . ?
C8 C7 C13 C14 -1.0(2) . . . . ?
C6 C7 C13 C14 175.94(15) . . . . ?
C7 C13 C14 C10 -0.4(2) . . . . ?
C9 C10 C14 C13 1.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H9 N1 0.93(3) 1.75(3) 2.591(3) 149(2) .
O1 H9 N1 0.93(3) 1.75(3) 2.591(3) 149(2) .

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1852254'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 (R)-2,2-difluoro-3-(1-phenylethyl)-2H-2l4,3l4-benzo[e][1,3,2]oxazaborinine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 B F2 N O'
_chemical_formula_sum            'C15 H14 B F2 N O'
_chemical_formula_weight         273.08

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   8.05(9)
_cell_length_b                   6.18(7)
_cell_length_c                   13.66(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.7(2)
_cell_angle_gamma                90
_cell_volume                     654(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.629
_cell_measurement_theta_max      26.721

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   0.5537
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5933
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.629
_diffrn_reflns_theta_max         26.721
_diffrn_reflns_theta_full        25.243
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2681
_reflns_number_gt                2197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.941
_reflns_Friedel_fraction_full    0.981

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0718P)²+0.0963P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_chemical_absolute_configuration R
_refine_ls_number_reflns         2681
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
F1 F 0.6035(3) 0.1822(4) 0.17352(16) 0.0603(7) Uani 1 1 d . . . . .
F2 F 0.4066(3) 0.1087(3) 0.25643(19) 0.0536(6) Uani 1 1 d . . . . .
O1 O 0.6719(3) 0.2435(4) 0.34406(18) 0.0411(6) Uani 1 1 d . . . . .
N1 N 0.4586(3) 0.4739(4) 0.22774(18) 0.0279(6) Uani 1 1 d . . . . .
C1 C 0.8427(5) 0.5367(7) 0.5748(3) 0.0484(10) Uani 1 1 d . . . . .
H1 H 0.9241 0.5168 0.6390 0.058 Uiso 1 1 calc R U . . .
C2 C 0.8157(5) 0.3736(6) 0.5054(3) 0.0423(9) Uani 1 1 d . . . . .
H14 H 0.8784 0.2420 0.5209 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6963(4) 0.4008(5) 0.4122(2) 0.0322(7) Uani 1 1 d . . . . .
C4 C 0.3366(4) 0.5151(5) 0.1266(2) 0.0330(7) Uani 1 1 d . . . . .
H6 H 0.3077 0.3720 0.0920 0.040 Uiso 1 1 calc R U . . .
C5 C 0.1722(4) 0.6089(6) 0.1398(2) 0.0333(7) Uani 1 1 d . . . . .
C6 C 0.0761(4) 0.4855(6) 0.1886(3) 0.0409(8) Uani 1 1 d . . . . .
H13 H 0.1120 0.3423 0.2094 0.049 Uiso 1 1 calc R U . . .
C7 C -0.0704(5) 0.5672(8) 0.2073(3) 0.0584(12) Uani 1 1 d . . . . .
H10 H -0.1348 0.4805 0.2414 0.070 Uiso 1 1 calc R U . . .
C8 C -0.1240(5) 0.7698(8) 0.1779(4) 0.0614(12) Uani 1 1 d . . . . .
H2 H -0.2245 0.8264 0.1923 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4892(4) 0.6243(5) 0.2947(2) 0.0272(6) Uani 1 1 d . . . . .
H3 H 0.4305 0.7587 0.2792 0.033 Uiso 1 1 calc R U . . .
C10 C 0.6082(4) 0.5955(5) 0.3911(2) 0.0287(7) Uani 1 1 d . . . . .
C11 C 0.6376(5) 0.7596(6) 0.4630(2) 0.0370(8) Uani 1 1 d . . . . .
H4 H 0.5759 0.8921 0.4483 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7542(5) 0.7311(7) 0.5541(3) 0.0458(9) Uani 1 1 d . . . . .
H5 H 0.7753 0.8433 0.6035 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4269(5) 0.6471(8) 0.0644(2) 0.0480(10) Uani 1 1 d . . . . .
H8 H 0.4557 0.7897 0.0958 0.072 Uiso 1 1 calc R U . . .
H9 H 0.3511 0.6647 -0.0045 0.072 Uiso 1 1 calc R U . . .
H7 H 0.5330 0.5731 0.0612 0.072 Uiso 1 1 calc R U . . .
C14 C -0.0343(5) 0.8917(7) 0.1278(4) 0.0628(13) Uani 1 1 d . . . . .
H11 H -0.0741 1.0328 0.1055 0.075 Uiso 1 1 calc R U . . .
C15 C 0.1156(5) 0.8128(6) 0.1087(3) 0.0475(10) Uani 1 1 d . . . . .
H12 H 0.1785 0.9003 0.0740 0.057 Uiso 1 1 calc R U . . .
B1 B 0.5394(6) 0.2463(6) 0.2510(3) 0.0363(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.357(12) . ?
F2 B1 1.383(12) . ?
O1 C3 1.323(11) . ?
O1 B1 1.421(13) . ?
N1 C9 1.280(11) . ?
N1 C4 1.485(14) . ?
N1 B1 1.545(15) . ?
C1 C2 1.360(12) . ?
C1 C12 1.386(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(13) . ?
C2 H14 0.9500 . ?
C3 C10 1.387(13) . ?
C4 C5 1.499(15) . ?
C4 C13 1.501(11) . ?
C4 H6 1.0000 . ?
C5 C15 1.367(13) . ?
C5 C6 1.380(10) . ?
C6 C7 1.369(14) . ?
C6 H13 0.9500 . ?
C7 C8 1.349(14) . ?
C7 H10 0.9500 . ?
C8 C14 1.350(11) . ?
C8 H2 0.9500 . ?
C9 C10 1.415(13) . ?
C9 H3 0.9500 . ?
C10 C11 1.387(12) . ?
C11 C12 1.353(13) . ?
C11 H4 0.9500 . ?
C12 H5 0.9500 . ?
C13 H8 0.9800 . ?
C13 H9 0.9800 . ?
C13 H7 0.9800 . ?
C14 C15 1.390(15) . ?
C14 H11 0.9500 . ?
C15 H12 0.9500 . ?

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
C3 O1 B1 123.5(5) . . ?
C9 N1 C4 119.4(6) . . ?
C9 N1 B1 121.6(6) . . ?
C4 N1 B1 118.9(3) . . ?
C2 C1 C12 121.6(7) . . ?
C2 C1 H1 119.2 . . ?
C12 C1 H1 119.2 . . ?
C1 C2 C3 119.5(6) . . ?
C1 C2 H14 120.2 . . ?
C3 C2 H14 120.2 . . ?
O1 C3 C2 119.5(6) . . ?
O1 C3 C10 121.4(6) . . ?
C2 C3 C10 119.0(4) . . ?
N1 C4 C5 109.8(7) . . ?
N1 C4 C13 108.7(8) . . ?
C5 C4 C13 115.9(7) . . ?
N1 C4 H6 107.4 . . ?
C5 C4 H6 107.4 . . ?
C13 C4 H6 107.4 . . ?
C15 C5 C6 118.4(7) . . ?
C15 C5 C4 123.3(4) . . ?
C6 C5 C4 118.2(7) . . ?
C7 C6 C5 120.7(7) . . ?
C7 C6 H13 119.6 . . ?
C5 C6 H13 119.6 . . ?
C8 C7 C6 120.5(5) . . ?
C8 C7 H10 119.7 . . ?
C6 C7 H10 119.7 . . ?
C7 C8 C14 119.8(7) . . ?
C7 C8 H2 120.1 . . ?
C14 C8 H2 120.1 . . ?
N1 C9 C10 121.6(6) . . ?
N1 C9 H3 119.2 . . ?
C10 C9 H3 119.2 . . ?
C11 C10 C3 120.5(6) . . ?
C11 C10 C9 120.7(6) . . ?
C3 C10 C9 118.8(4) . . ?
C12 C11 C10 120.0(6) . . ?
C12 C11 H4 120.0 . . ?
C10 C11 H4 120.0 . . ?
C11 C12 C1 119.4(4) . . ?
C11 C12 H5 120.3 . . ?
C1 C12 H5 120.3 . . ?
C4 C13 H8 109.5 . . ?
C4 C13 H9 109.5 . . ?
H8 C13 H9 109.5 . . ?
C4 C13 H7 109.5 . . ?
H8 C13 H7 109.5 . . ?
H9 C13 H7 109.5 . . ?
C8 C14 C15 120.6(7) . . ?
C8 C14 H11 119.7 . . ?
C15 C14 H11 119.7 . . ?
C5 C15 C14 119.9(5) . . ?
C5 C15 H12 120.1 . . ?
C14 C15 H12 120.1 . . ?
F1 B1 F2 108.9(6) . . ?
F1 B1 O1 110.0(9) . . ?
F2 B1 O1 110.4(7) . . ?
F1 B1 N1 109.4(5) . . ?
F2 B1 N1 106.4(8) . . ?
O1 B1 N1 111.6(4) . . ?

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
C12 C1 C2 C3 -0.5(6) . . . . ?
B1 O1 C3 C2 172.8(3) . . . . ?
B1 O1 C3 C10 -9.2(5) . . . . ?
C1 C2 C3 O1 179.0(3) . . . . ?
C1 C2 C3 C10 0.8(5) . . . . ?
C9 N1 C4 C5 -50.0(4) . . . . ?
B1 N1 C4 C5 127.3(3) . . . . ?
C9 N1 C4 C13 77.7(7) . . . . ?
B1 N1 C4 C13 -105.0(6) . . . . ?
N1 C4 C5 C15 115.8(5) . . . . ?
C13 C4 C5 C15 -7.7(5) . . . . ?
N1 C4 C5 C6 -62.1(5) . . . . ?
C13 C4 C5 C6 174.3(3) . . . . ?
C15 C5 C6 C7 -1.4(5) . . . . ?
C4 C5 C6 C7 176.6(3) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C6 C7 C8 C14 1.2(6) . . . . ?
C4 N1 C9 C10 -178.1(3) . . . . ?
B1 N1 C9 C10 4.6(5) . . . . ?
O1 C3 C10 C11 -179.0(3) . . . . ?
C2 C3 C10 C11 -0.9(5) . . . . ?
O1 C3 C10 C9 0.4(4) . . . . ?
C2 C3 C10 C9 178.5(3) . . . . ?
N1 C9 C10 C11 -179.1(3) . . . . ?
N1 C9 C10 C3 1.5(4) . . . . ?
C3 C10 C11 C12 0.6(5) . . . . ?
C9 C10 C11 C12 -178.7(3) . . . . ?
C10 C11 C12 C1 -0.3(6) . . . . ?
C2 C1 C12 C11 0.3(6) . . . . ?
C7 C8 C14 C15 -1.7(6) . . . . ?
C6 C5 C15 C14 0.9(5) . . . . ?
C4 C5 C15 C14 -177.0(3) . . . . ?
C8 C14 C15 C5 0.7(6) . . . . ?
C3 O1 B1 F1 135.6(3) . . . . ?
C3 O1 B1 F2 -104.2(8) . . . . ?
C3 O1 B1 N1 13.9(5) . . . . ?
C9 N1 B1 F1 -133.7(7) . . . . ?
C4 N1 B1 F1 49.0(8) . . . . ?
C9 N1 B1 F2 108.7(6) . . . . ?
C4 N1 B1 F2 -68.5(6) . . . . ?
C9 N1 B1 O1 -11.7(5) . . . . ?
C4 N1 B1 O1 171.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H3 F2 0.95 2.19 3.08(3) 156.3 1_565
C13 H9 F1 0.98 2.44 3.20(4) 134.5 2_655

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1852253'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 (S,E)-2-(((1-phenylethyl)imino)methyl)phenol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   18.227(18)
_cell_length_b                   5.852(4)
_cell_length_c                   14.53(2)
_cell_angle_alpha                90
_cell_angle_beta                 128.30(9)
_cell_angle_gamma                90
_cell_volume                     1216(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.235
_cell_measurement_theta_max      26.429

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   0.6713
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4864
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_full        25.243
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_point_group_measured_fraction_full 0.855
_reflns_number_total             2120
_reflns_number_gt                1812
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.572
_reflns_Friedel_fraction_max     0.689
_reflns_Friedel_fraction_full    0.694

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.7768P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(10)
_chemical_absolute_configuration S
_refine_ls_number_reflns         2120
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.124
_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
O1 O 0.38223(15) 0.7326(4) 0.4629(2) 0.0390(6) Uani 1 1 d . . . . .
N1 N 0.45244(15) 0.3974(4) 0.6116(2) 0.0287(6) Uani 1 1 d . . . . .
C1 C 0.1453(2) 0.5711(7) 0.2186(3) 0.0386(8) Uani 1 1 d . . . . .
H1 H 0.0949 0.6306 0.1442 0.046 Uiso 1 1 calc R U . . .
C2 C 0.2274(2) 0.6940(6) 0.2883(3) 0.0340(7) Uani 1 1 d . . . . .
H5 H 0.2328 0.8365 0.2617 0.041 Uiso 1 1 calc R U . . .
C3 C 0.30227(19) 0.6101(5) 0.3976(3) 0.0288(6) Uani 1 1 d . . . . .
C4 C 0.29414(18) 0.3951(5) 0.4354(2) 0.0253(6) Uani 1 1 d . . . . .
C5 C 0.37361(18) 0.2942(5) 0.5454(2) 0.0263(6) Uani 1 1 d . . . . .
H14 H 0.3667 0.1489 0.5684 0.032 Uiso 1 1 calc R U . . .
C6 C 0.53215(18) 0.2812(5) 0.7170(2) 0.0280(6) Uani 1 1 d . . . . .
H6 H 0.5090 0.1430 0.7325 0.034 Uiso 1 1 calc R U . . .
C7 C 0.57707(18) 0.4431(5) 0.8204(2) 0.0268(6) Uani 1 1 d . . . . .
C8 C 0.57480(19) 0.3947(6) 0.9118(2) 0.0314(7) Uani 1 1 d . . . . .
H9 H 0.5474 0.2560 0.9112 0.038 Uiso 1 1 calc R U . . .
C9 C 0.6122(2) 0.5470(7) 1.0049(3) 0.0371(8) Uani 1 1 d . . . . .
H8 H 0.6090 0.5132 1.0663 0.044 Uiso 1 1 calc R U . . .
C10 C 0.65420(19) 0.7478(6) 1.0081(3) 0.0354(7) Uani 1 1 d . . . . .
H2 H 0.6795 0.8523 1.0711 0.042 Uiso 1 1 calc R U . . .
C11 C 0.1346(2) 0.3613(6) 0.2549(3) 0.0362(8) Uani 1 1 d . . . . .
H3 H 0.0775 0.2789 0.2066 0.043 Uiso 1 1 calc R U . . .
C12 C 0.20951(19) 0.2761(6) 0.3633(2) 0.0310(7) Uani 1 1 d . . . . .
H15 H 0.2031 0.1338 0.3891 0.037 Uiso 1 1 calc R U . . .
C13 C 0.6197(2) 0.6453(5) 0.8248(3) 0.0325(7) Uani 1 1 d . . . . .
H7 H 0.6220 0.6815 0.7629 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6587(2) 0.7937(6) 0.9187(3) 0.0358(7) Uani 1 1 d . . . . .
H10 H 0.6889 0.9288 0.9215 0.043 Uiso 1 1 calc R U . . .
C15 C 0.5984(2) 0.2062(6) 0.6921(3) 0.0357(7) Uani 1 1 d . . . . .
H11 H 0.5676 0.0907 0.6299 0.054 Uiso 1 1 calc R U . . .
H13 H 0.6552 0.1413 0.7635 0.054 Uiso 1 1 calc R U . . .
H12 H 0.6150 0.3385 0.6670 0.054 Uiso 1 1 calc R U . . .
H4 H 0.426(3) 0.653(8) 0.532(3) 0.054 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
O1 C3 1.350(4) . ?
O1 H4 0.93(4) . ?
N1 C5 1.281(4) . ?
N1 C6 1.470(4) . ?
C1 C2 1.379(5) . ?
C1 C11 1.397(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(5) . ?
C2 H5 0.9500 . ?
C3 C4 1.417(4) . ?
C4 C12 1.399(4) . ?
C4 C5 1.460(5) . ?
C5 H14 0.9500 . ?
C6 C7 1.516(5) . ?
C6 C15 1.524(4) . ?
C6 H6 1.0000 . ?
C7 C8 1.384(5) . ?
C7 C13 1.395(4) . ?
C8 C9 1.395(5) . ?
C8 H9 0.9500 . ?
C9 C10 1.387(5) . ?
C9 H8 0.9500 . ?
C10 C14 1.378(5) . ?
C10 H2 0.9500 . ?
C11 C12 1.388(5) . ?
C11 H3 0.9500 . ?
C12 H15 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H7 0.9500 . ?
C14 H10 0.9500 . ?
C15 H11 0.9800 . ?
C15 H13 0.9800 . ?
C15 H12 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
C3 O1 H4 109(3) . . ?
C5 N1 C6 119.2(3) . . ?
C2 C1 C11 121.5(3) . . ?
C2 C1 H1 119.2 . . ?
C11 C1 H1 119.2 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H5 119.9 . . ?
C3 C2 H5 119.9 . . ?
O1 C3 C2 118.8(3) . . ?
O1 C3 C4 121.7(3) . . ?
C2 C3 C4 119.4(3) . . ?
C12 C4 C3 118.9(3) . . ?
C12 C4 C5 120.3(3) . . ?
C3 C4 C5 120.8(3) . . ?
N1 C5 C4 121.4(3) . . ?
N1 C5 H14 119.3 . . ?
C4 C5 H14 119.3 . . ?
N1 C6 C7 108.8(3) . . ?
N1 C6 C15 107.6(3) . . ?
C7 C6 C15 113.2(3) . . ?
N1 C6 H6 109.1 . . ?
C7 C6 H6 109.1 . . ?
C15 C6 H6 109.1 . . ?
C8 C7 C13 118.5(3) . . ?
C8 C7 C6 120.3(3) . . ?
C13 C7 C6 121.2(3) . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H9 119.6 . . ?
C9 C8 H9 119.6 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H8 120.0 . . ?
C8 C9 H8 120.0 . . ?
C14 C10 C9 119.2(3) . . ?
C14 C10 H2 120.4 . . ?
C9 C10 H2 120.4 . . ?
C12 C11 C1 118.3(3) . . ?
C12 C11 H3 120.8 . . ?
C1 C11 H3 120.8 . . ?
C11 C12 C4 121.6(3) . . ?
C11 C12 H15 119.2 . . ?
C4 C12 H15 119.2 . . ?
C14 C13 C7 120.5(3) . . ?
C14 C13 H7 119.7 . . ?
C7 C13 H7 119.7 . . ?
C10 C14 C13 120.8(3) . . ?
C10 C14 H10 119.6 . . ?
C13 C14 H10 119.6 . . ?
C6 C15 H11 109.5 . . ?
C6 C15 H13 109.5 . . ?
H11 C15 H13 109.5 . . ?
C6 C15 H12 109.5 . . ?
H11 C15 H12 109.5 . . ?
H13 C15 H12 109.5 . . ?

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
C11 C1 C2 C3 0.1(5) . . . . ?
C1 C2 C3 O1 178.9(3) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
O1 C3 C4 C12 -179.6(3) . . . . ?
C2 C3 C4 C12 -2.2(4) . . . . ?
O1 C3 C4 C5 -2.1(4) . . . . ?
C2 C3 C4 C5 175.3(3) . . . . ?
C6 N1 C5 C4 -175.6(2) . . . . ?
C12 C4 C5 N1 178.3(3) . . . . ?
C3 C4 C5 N1 0.8(4) . . . . ?
C5 N1 C6 C7 -131.4(3) . . . . ?
C5 N1 C6 C15 105.6(3) . . . . ?
N1 C6 C7 C8 114.2(3) . . . . ?
C15 C6 C7 C8 -126.3(3) . . . . ?
N1 C6 C7 C13 -64.5(3) . . . . ?
C15 C6 C7 C13 55.0(4) . . . . ?
C13 C7 C8 C9 1.5(4) . . . . ?
C6 C7 C8 C9 -177.2(3) . . . . ?
C7 C8 C9 C10 -1.4(4) . . . . ?
C8 C9 C10 C14 -0.3(4) . . . . ?
C2 C1 C11 C12 -0.8(5) . . . . ?
C1 C11 C12 C4 -0.1(4) . . . . ?
C3 C4 C12 C11 1.6(4) . . . . ?
C5 C4 C12 C11 -176.0(3) . . . . ?
C8 C7 C13 C14 -0.1(4) . . . . ?
C6 C7 C13 C14 178.6(3) . . . . ?
C9 C10 C14 C13 1.8(4) . . . . ?
C7 C13 C14 C10 -1.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H4 N1 0.93(4) 1.76(4) 2.593(4) 146(4) .
O1 H4 N1 0.93(4) 1.76(4) 2.593(4) 146(4) .
O1 H4 N1 0.93(4) 1.76(4) 2.593(4) 146(4) .

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1852256'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 3-benzyl-2,2-difluoro-2H-2l4,3l4-benzo[e][1,3,2]oxazaborinine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 B F2 N O'
_chemical_formula_sum            'C14 H12 B F2 N O'
_chemical_formula_weight         259.06

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   7.0179(7)
_cell_length_b                   11.9206(11)
_cell_length_c                   28.844(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2413.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      1.412
_cell_measurement_theta_max      28.698

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   0.7037
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14168
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.412
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3115
_reflns_number_gt                1883
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3115
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_restrained_S_all      0.889
_refine_ls_shift/su_max          0.001
_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
C12 C -0.3965(2) 1.18597(13) 0.03044(5) 0.0366(4) Uani 1 1 d . . . . .
H12 H -0.5169 1.1866 0.0154 0.044 Uiso 1 1 calc R U . . .
B1 B 0.1503(2) 1.01230(13) 0.15465(5) 0.0249(4) Uani 1 1 d . . . . .
C11 C -0.2730(2) 1.09707(13) 0.02394(5) 0.0367(4) Uani 1 1 d . . . . .
H11 H -0.3086 1.0363 0.0045 0.044 Uiso 1 1 calc R U . . .
F1 F -0.01633(12) 0.96458(6) 0.13754(3) 0.0357(2) Uani 1 1 d . . . . .
F2 F 0.30428(12) 0.96853(7) 0.13037(3) 0.0383(2) Uani 1 1 d . . . . .
N1 N 0.14145(15) 1.14232(9) 0.14587(4) 0.0218(3) Uani 1 1 d . . . . .
O1 O 0.17166(13) 0.98846(7) 0.20368(3) 0.0269(2) Uani 1 1 d . . . . .
C07 C 0.12456(18) 1.21300(11) 0.17955(4) 0.0230(3) Uani 1 1 d . . . . .
H07 H 0.1144 1.2906 0.1726 0.028 Uiso 1 1 calc R U . . .
C06 C 0.12068(18) 1.17840(11) 0.22687(4) 0.0210(3) Uani 1 1 d . . . . .
C01 C 0.14977(18) 1.06482(11) 0.23756(4) 0.0211(3) Uani 1 1 d . . . . .
C08 C 0.1499(2) 1.18494(11) 0.09765(4) 0.0274(3) Uani 1 1 d . . . . .
H08A H 0.2387 1.1377 0.0795 0.033 Uiso 1 1 calc R U . . .
H08B H 0.2010 1.2624 0.0979 0.033 Uiso 1 1 calc R U . . .
C04 C 0.10688(19) 1.22343(12) 0.30829(5) 0.0277(3) Uani 1 1 d . . . . .
H04 H 0.0910 1.2765 0.3325 0.033 Uiso 1 1 calc R U . . .
C02 C 0.15955(19) 1.03214(11) 0.28385(5) 0.0251(3) Uani 1 1 d . . . . .
H02 H 0.1804 0.9556 0.2915 0.030 Uiso 1 1 calc R U . . .
C03 C 0.13906(19) 1.11078(11) 0.31846(5) 0.0270(3) Uani 1 1 d . . . . .
H03 H 0.1470 1.0877 0.3499 0.032 Uiso 1 1 calc R U . . .
C05 C 0.09847(19) 1.25683(12) 0.26277(5) 0.0266(3) Uani 1 1 d . . . . .
H05 H 0.0775 1.3336 0.2555 0.032 Uiso 1 1 calc R U . . .
C13 C -0.3442(2) 1.27408(13) 0.05894(5) 0.0353(4) Uani 1 1 d . . . . .
H13 H -0.4295 1.3348 0.0638 0.042 Uiso 1 1 calc R U . . .
C09 C -0.0425(2) 1.18496(11) 0.07430(4) 0.0243(3) Uani 1 1 d . . . . .
C14 C -0.1678(2) 1.27390(12) 0.08041(5) 0.0308(4) Uani 1 1 d . . . . .
H14 H -0.1321 1.3353 0.0995 0.037 Uiso 1 1 calc R U . . .
C10 C -0.0969(2) 1.09648(12) 0.04582(5) 0.0309(4) Uani 1 1 d . . . . .
H10 H -0.0127 1.0350 0.0413 0.037 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
C12 C11 1.382(2) . ?
C12 C13 1.383(2) . ?
B1 F2 1.3895(17) . ?
B1 F1 1.3908(17) . ?
B1 O1 1.4501(17) . ?
B1 N1 1.5717(18) . ?
C11 C10 1.388(2) . ?
N1 C07 1.2913(15) . ?
N1 C08 1.4820(15) . ?
O1 C01 1.3443(14) . ?
C07 C06 1.4263(17) . ?
C06 C01 1.4035(17) . ?
C06 C05 1.4038(17) . ?
C01 C02 1.3927(17) . ?
C08 C09 1.5091(19) . ?
C04 C05 1.3733(18) . ?
C04 C03 1.3930(18) . ?
C02 C03 1.3770(17) . ?
C13 C14 1.3838(19) . ?
C09 C14 1.3887(19) . ?
C09 C10 1.3903(18) . ?

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
C11 C12 C13 119.76(14) . . ?
F2 B1 F1 108.74(11) . . ?
F2 B1 O1 109.73(12) . . ?
F1 B1 O1 110.67(12) . . ?
F2 B1 N1 108.64(11) . . ?
F1 B1 N1 108.23(11) . . ?
O1 B1 N1 110.77(11) . . ?
C12 C11 C10 120.05(14) . . ?
C07 N1 C08 119.08(11) . . ?
C07 N1 B1 121.72(11) . . ?
C08 N1 B1 119.20(10) . . ?
C01 O1 B1 124.35(10) . . ?
N1 C07 C06 122.21(12) . . ?
C01 C06 C05 119.78(12) . . ?
C01 C06 C07 119.10(12) . . ?
C05 C06 C07 121.03(12) . . ?
O1 C01 C02 120.12(12) . . ?
O1 C01 C06 120.68(11) . . ?
C02 C01 C06 119.18(11) . . ?
N1 C08 C09 112.52(10) . . ?
C05 C04 C03 119.21(13) . . ?
C03 C02 C01 119.97(12) . . ?
C02 C03 C04 121.36(13) . . ?
C04 C05 C06 120.48(13) . . ?
C12 C13 C14 120.14(14) . . ?
C14 C09 C10 118.72(14) . . ?
C14 C09 C08 120.67(13) . . ?
C10 C09 C08 120.61(13) . . ?
C13 C14 C09 120.71(14) . . ?
C11 C10 C09 120.62(14) . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1852255'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
(S)-2,2-difluoro-3-(1-phenylethyl)-2H-2l4,3l4-benzo[e][1,3,2]oxazaborinine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 B F2 N O'
_chemical_formula_sum            'C15 H14 B F2 N O'
_chemical_formula_weight         273.08

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   8.1632(11)
_cell_length_b                   6.2464(7)
_cell_length_c                   13.8361(16)
_cell_angle_alpha                90
_cell_angle_beta                 105.594(7)
_cell_angle_gamma                90
_cell_volume                     679.54(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      1.528
_cell_measurement_theta_max      30.139

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   0.4762
_exptl_transmission_factor_max   0.7460
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10694
_diffrn_reflns_av_unetI/netI     0.0976
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.528
_diffrn_reflns_theta_max         30.139
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4003
_reflns_number_gt                2760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0271P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_chemical_absolute_configuration S
_refine_ls_number_reflns         4003
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
O1 O 0.8279(3) 0.3167(4) 0.15584(16) 0.0410(6) Uani 1 1 d . . . . .
C07 C 1.0108(3) -0.0647(5) 0.20534(18) 0.0269(6) Uani 1 1 d . . . . .
H07 H 1.0681 -0.1979 0.2206 0.032 Uiso 1 1 calc R U . . .
N1 N 1.0419(3) 0.0859(4) 0.27188(15) 0.0273(5) Uani 1 1 d . . . . .
C06 C 0.8915(4) -0.0352(5) 0.10894(19) 0.0278(6) Uani 1 1 d . . . . .
F1A F 1.0929(3) 0.4514(3) 0.24351(17) 0.0543(6) Uani 1 1 d . . . . .
C05 C 0.8625(4) -0.2002(6) 0.0372(2) 0.0369(7) Uani 1 1 d . . . . .
H05 H 0.9231 -0.3313 0.0517 0.044 Uiso 1 1 calc R U . . .
C10 C 1.3278(4) -0.0488(5) 0.3600(2) 0.0332(7) Uani 1 1 d . . . . .
C01 C 0.8037(4) 0.1588(5) 0.0879(2) 0.0327(7) Uani 1 1 d . . . . .
C08 C 1.1639(4) 0.0451(5) 0.37325(19) 0.0333(7) Uani 1 1 d . . . . .
H08 H 1.1921 0.1867 0.4074 0.040 Uiso 1 1 calc R U . . .
F1B F 0.8962(3) 0.3773(4) 0.32643(14) 0.0604(7) Uani 1 1 d . . . . .
C04 C 0.7452(4) -0.1703(6) -0.0545(2) 0.0462(9) Uani 1 1 d . . . . .
H04 H 0.7245 -0.2809 -0.1034 0.055 Uiso 1 1 calc R U . . .
C02 C 0.6845(4) 0.1864(6) -0.0057(2) 0.0438(8) Uani 1 1 d . . . . .
H02 H 0.6233 0.3169 -0.0211 0.053 Uiso 1 1 calc R U . . .
C15 C 1.4243(4) 0.0745(6) 0.3113(2) 0.0407(8) Uani 1 1 d . . . . .
H15 H 1.3886 0.2158 0.2903 0.049 Uiso 1 1 calc R U . . .
C03 C 0.6574(4) 0.0228(6) -0.0748(2) 0.0480(9) Uani 1 1 d . . . . .
H03 H 0.5768 0.0421 -0.1380 0.058 Uiso 1 1 calc R U . . .
C09 C 1.0733(5) -0.0881(7) 0.4356(2) 0.0463(9) Uani 1 1 d . . . . .
H09A H 0.9690 -0.0146 0.4392 0.069 Uiso 1 1 calc R U . . .
H09B H 1.1482 -0.1066 0.5035 0.069 Uiso 1 1 calc R U . . .
H09C H 1.0443 -0.2286 0.4042 0.069 Uiso 1 1 calc R U . . .
C11 C 1.3842(4) -0.2527(6) 0.3914(2) 0.0459(9) Uani 1 1 d . . . . .
H11 H 1.3222 -0.3385 0.4260 0.055 Uiso 1 1 calc R U . . .
C12 C 1.5329(5) -0.3325(7) 0.3723(3) 0.0615(12) Uani 1 1 d . . . . .
H12 H 1.5711 -0.4726 0.3940 0.074 Uiso 1 1 calc R U . . .
B1 B 0.9610(5) 0.3148(6) 0.2491(3) 0.0358(8) Uani 1 1 d . . . . .
C14 C 1.5701(5) -0.0057(7) 0.2933(3) 0.0570(11) Uani 1 1 d . . . . .
H14 H 1.6344 0.0806 0.2604 0.068 Uiso 1 1 calc R U . . .
C13 C 1.6234(5) -0.2105(8) 0.3226(3) 0.0626(12) Uani 1 1 d . . . . .
H13 H 1.7226 -0.2667 0.3085 0.075 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
O1 C01 1.339(4) . ?
O1 B1 1.446(4) . ?
C07 N1 1.293(3) . ?
C07 C06 1.436(3) . ?
N1 C08 1.508(3) . ?
N1 B1 1.571(4) . ?
C06 C01 1.398(4) . ?
C06 C05 1.406(4) . ?
F1A B1 1.392(4) . ?
C05 C04 1.381(4) . ?
C10 C11 1.384(5) . ?
C10 C15 1.398(4) . ?
C10 C08 1.516(4) . ?
C01 C02 1.406(4) . ?
C08 C09 1.525(4) . ?
F1B B1 1.371(4) . ?
C04 C03 1.393(5) . ?
C02 C03 1.376(5) . ?
C15 C14 1.374(5) . ?
C11 C12 1.402(5) . ?
C12 C13 1.368(6) . ?
C14 C13 1.377(6) . ?

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
C01 O1 B1 123.6(2) . . ?
N1 C07 C06 121.5(3) . . ?
C07 N1 C08 119.6(2) . . ?
C07 N1 B1 121.9(2) . . ?
C08 N1 B1 118.5(2) . . ?
C01 C06 C05 120.6(2) . . ?
C01 C06 C07 119.1(3) . . ?
C05 C06 C07 120.3(3) . . ?
C04 C05 C06 119.5(3) . . ?
C11 C10 C15 118.4(3) . . ?
C11 C10 C08 123.2(3) . . ?
C15 C10 C08 118.4(3) . . ?
O1 C01 C06 121.4(2) . . ?
O1 C01 C02 119.4(3) . . ?
C06 C01 C02 119.1(3) . . ?
N1 C08 C10 109.7(2) . . ?
N1 C08 C09 108.6(2) . . ?
C10 C08 C09 115.8(3) . . ?
C05 C04 C03 119.6(3) . . ?
C03 C02 C01 119.4(3) . . ?
C14 C15 C10 120.9(4) . . ?
C02 C03 C04 121.7(3) . . ?
C10 C11 C12 120.0(4) . . ?
C13 C12 C11 120.6(4) . . ?
F1B B1 F1A 109.6(3) . . ?
F1B B1 O1 109.8(3) . . ?
F1A B1 O1 110.6(3) . . ?
F1B B1 N1 109.4(3) . . ?
F1A B1 N1 106.2(3) . . ?
O1 B1 N1 111.1(3) . . ?
C15 C14 C13 120.4(4) . . ?
C12 C13 C14 119.7(4) . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_preparation       Luminescent
