# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_4a_15srv002
_database_code_depnum_ccdc_archive 'CCDC 1551614'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2015-01-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 Bis-3,4,5-trifluorophenylborinic acid benzylamine complex  
;
_chemical_formula_moiety         'C19 H14 B F6 N O'
_chemical_formula_sum            'C19 H14 B F6 N O'
_chemical_formula_weight         397.12
_chemical_melting_point          393(2)
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.03430(10)
_cell_length_b                   10.2063(2)
_cell_length_c                   11.0348(2)
_cell_angle_alpha                66.3381(18)
_cell_angle_beta                 70.1856(17)
_cell_angle_gamma                78.1262(19)
_cell_volume                     873.89(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.50
_cell_measurement_theta_min      2.19
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1035 before and 0.0427 after correction.
The Ratio of minimum to maximum transmission is 0.9474.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18051
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.10
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'iMuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3848
_reflns_number_total             4649
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1073
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F -0.20075(12) 0.66672(10) 0.16511(11) 0.0412(3) Uani 1 d . . .
F2 F 0.04691(13) 0.77102(9) -0.05566(9) 0.0335(2) Uani 1 d . . .
F3 F 0.32604(12) 0.61085(11) -0.08381(9) 0.0396(3) Uani 1 d . . .
F4 F 0.63163(11) 0.26659(10) 0.38904(10) 0.0334(2) Uani 1 d . . .
F5 F 0.77197(9) 0.03468(11) 0.32070(9) 0.0330(2) Uani 1 d . . .
F6 F 0.60311(10) -0.12271(10) 0.27953(10) 0.0308(2) Uani 1 d . . .
O1 O 0.05580(11) 0.10150(9) 0.31688(9) 0.01477(19) Uani 1 d . . .
N1 N -0.00144(13) 0.18774(11) 0.50154(11) 0.0135(2) Uani 1 d . . .
C1 C 0.01192(16) 0.27091(14) 0.58187(14) 0.0184(3) Uani 1 d . . .
C2 C -0.13048(17) 0.25231(15) 0.70628(14) 0.0214(3) Uani 1 d . . .
C3 C -0.1303(2) 0.13788(17) 0.82935(15) 0.0285(3) Uani 1 d . . .
C4 C -0.2675(3) 0.1112(2) 0.93912(18) 0.0418(5) Uani 1 d . . .
C5 C -0.4036(2) 0.1987(2) 0.9268(2) 0.0473(5) Uani 1 d . . .
C6 C -0.4049(2) 0.3141(2) 0.8063(2) 0.0443(5) Uani 1 d . . .
C7 C -0.26766(19) 0.34075(18) 0.69556(18) 0.0313(3) Uani 1 d . . .
C8 C 0.09581(15) 0.36735(13) 0.24121(12) 0.0143(2) Uani 1 d . . .
C9 C -0.04806(16) 0.45144(14) 0.25229(14) 0.0195(3) Uani 1 d . . .
C10 C -0.06249(17) 0.58543(14) 0.15298(15) 0.0227(3) Uani 1 d . . .
C11 C 0.06228(19) 0.63966(14) 0.04019(14) 0.0227(3) Uani 1 d . . .
C12 C 0.20382(18) 0.55781(15) 0.02747(13) 0.0229(3) Uani 1 d . . .
C13 C 0.22200(16) 0.42413(14) 0.12590(13) 0.0192(3) Uani 1 d . . .
C14 C 0.29679(14) 0.15348(13) 0.35124(12) 0.0139(2) Uani 1 d . . .
C15 C 0.38706(16) 0.23236(14) 0.37516(13) 0.0180(3) Uani 1 d . . .
C16 C 0.54424(16) 0.19097(15) 0.36580(14) 0.0220(3) Uani 1 d . . .
C17 C 0.61746(15) 0.07319(16) 0.33190(13) 0.0220(3) Uani 1 d . . .
C18 C 0.52957(15) -0.00580(15) 0.31023(13) 0.0202(3) Uani 1 d . . .
C19 C 0.37194(15) 0.03288(14) 0.31846(13) 0.0161(2) Uani 1 d . . .
B1 B 0.11586(16) 0.20366(14) 0.34713(14) 0.0124(2) Uani 1 d . . .
H1 H 0.016(2) 0.140(2) 0.257(2) 0.035(5) Uiso 1 d . . .
H1A H -0.102(2) 0.2086(18) 0.4936(17) 0.020(4) Uiso 1 d . . .
H1B H -0.001(2) 0.0922(19) 0.5553(18) 0.023(4) Uiso 1 d . . .
H1C H 0.0227(19) 0.3710(18) 0.5185(17) 0.021(4) Uiso 1 d . . .
H1D H 0.110(2) 0.2338(18) 0.6113(17) 0.022(4) Uiso 1 d . . .
H3 H -0.035(2) 0.077(2) 0.8367(19) 0.033(5) Uiso 1 d . . .
H4 H -0.267(3) 0.026(3) 1.025(3) 0.062(7) Uiso 1 d . . .
H5 H -0.498(3) 0.182(3) 1.000(3) 0.061(7) Uiso 1 d . . .
H6 H -0.495(3) 0.377(3) 0.793(2) 0.053(6) Uiso 1 d . . .
H7 H -0.266(2) 0.416(2) 0.610(2) 0.035(5) Uiso 1 d . . .
H9 H -0.140(2) 0.4197(19) 0.3261(19) 0.027(4) Uiso 1 d . . .
H13 H 0.322(2) 0.3737(19) 0.1124(18) 0.026(4) Uiso 1 d . . .
H15 H 0.3441(18) 0.3166(17) 0.3971(16) 0.015(4) Uiso 1 d . . .
H19 H 0.3159(19) -0.0218(18) 0.2975(17) 0.022(4) Uiso 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 C10 1.3475(17) . ?
F2 C11 1.3491(14) . ?
F3 C12 1.3465(16) . ?
F4 C16 1.3533(15) . ?
F5 C17 1.3470(15) . ?
F6 C18 1.3511(16) . ?
O1 B1 1.4588(16) . ?
O1 H1 0.78(2) . ?
N1 C1 1.4965(16) . ?
N1 B1 1.6362(17) . ?
N1 H1A 0.912(17) . ?
N1 H1B 0.915(18) . ?
C1 C2 1.5066(18) . ?
C1 H1C 0.982(17) . ?
C1 H1D 0.995(17) . ?
C2 C3 1.391(2) . ?
C2 C7 1.385(2) . ?
C3 C4 1.391(2) . ?
C3 H3 0.96(2) . ?
C4 C5 1.375(3) . ?
C4 H4 0.99(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.94(2) . ?
C6 C7 1.396(2) . ?
C6 H6 0.94(2) . ?
C7 H7 0.95(2) . ?
C8 C9 1.3993(18) . ?
C8 C13 1.3968(18) . ?
C8 B1 1.6253(17) . ?
C9 C10 1.3815(18) . ?
C9 H9 0.948(18) . ?
C10 C11 1.371(2) . ?
C11 C12 1.373(2) . ?
C12 C13 1.3811(18) . ?
C13 H13 0.942(18) . ?
C14 C15 1.4034(17) . ?
C14 C19 1.3978(18) . ?
C14 B1 1.6196(18) . ?
C15 C16 1.3764(19) . ?
C15 H15 0.957(16) . ?
C16 C17 1.374(2) . ?
C17 C18 1.373(2) . ?
C18 C19 1.3791(18) . ?
C19 H19 0.959(17) . ?

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 H1 111.9(15) . . ?
C1 N1 B1 122.88(10) . . ?
C1 N1 H1A 106.6(10) . . ?
C1 N1 H1B 108.8(11) . . ?
B1 N1 H1A 106.3(10) . . ?
B1 N1 H1B 107.9(11) . . ?
H1A N1 H1B 102.6(15) . . ?
N1 C1 C2 109.18(10) . . ?
N1 C1 H1C 106.9(10) . . ?
N1 C1 H1D 108.6(10) . . ?
C2 C1 H1C 113.4(10) . . ?
C2 C1 H1D 110.2(10) . . ?
H1C C1 H1D 108.5(13) . . ?
C3 C2 C1 120.21(13) . . ?
C7 C2 C1 120.26(13) . . ?
C7 C2 C3 119.26(14) . . ?
C2 C3 H3 119.2(11) . . ?
C4 C3 C2 120.17(17) . . ?
C4 C3 H3 120.6(11) . . ?
C3 C4 H4 119.1(15) . . ?
C5 C4 C3 120.07(18) . . ?
C5 C4 H4 120.8(15) . . ?
C4 C5 C6 120.43(16) . . ?
C4 C5 H5 121.0(15) . . ?
C6 C5 H5 118.6(15) . . ?
C5 C6 C7 119.69(19) . . ?
C5 C6 H6 123.4(15) . . ?
C7 C6 H6 116.9(15) . . ?
C2 C7 C6 120.36(18) . . ?
C2 C7 H7 118.1(12) . . ?
C6 C7 H7 121.5(12) . . ?
C9 C8 B1 122.87(11) . . ?
C13 C8 C9 117.27(11) . . ?
C13 C8 B1 119.58(11) . . ?
C8 C9 H9 122.5(11) . . ?
C10 C9 C8 120.72(13) . . ?
C10 C9 H9 116.8(11) . . ?
F1 C10 C9 120.46(13) . . ?
F1 C10 C11 118.16(12) . . ?
C11 C10 C9 121.38(13) . . ?
F2 C11 C10 120.80(13) . . ?
F2 C11 C12 120.68(13) . . ?
C10 C11 C12 118.52(12) . . ?
F3 C12 C11 118.46(12) . . ?
F3 C12 C13 120.22(13) . . ?
C11 C12 C13 121.32(13) . . ?
C8 C13 H13 121.7(11) . . ?
C12 C13 C8 120.80(13) . . ?
C12 C13 H13 117.5(11) . . ?
C15 C14 B1 122.96(11) . . ?
C19 C14 C15 117.74(11) . . ?
C19 C14 B1 119.08(11) . . ?
C14 C15 H15 122.5(9) . . ?
C16 C15 C14 120.33(13) . . ?
C16 C15 H15 117.1(9) . . ?
F4 C16 C15 120.51(14) . . ?
F4 C16 C17 118.03(12) . . ?
C17 C16 C15 121.46(13) . . ?
F5 C17 C16 121.14(13) . . ?
F5 C17 C18 120.24(13) . . ?
C18 C17 C16 118.61(12) . . ?
F6 C18 C17 117.68(12) . . ?
F6 C18 C19 120.93(13) . . ?
C17 C18 C19 121.39(13) . . ?
C14 C19 H19 120.5(10) . . ?
C18 C19 C14 120.44(12) . . ?
C18 C19 H19 119.0(10) . . ?
O1 B1 N1 101.20(9) . . ?
O1 B1 C8 112.32(10) . . ?
O1 B1 C14 109.92(10) . . ?
C8 B1 N1 109.68(10) . . ?
C14 B1 N1 110.77(10) . . ?
C14 B1 C8 112.41(10) . . ?

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 H1 F2 0.78(2) 2.26(2) 3.0280(12) 166.3(19) 2_565
N1 H1B O1 0.915(18) 1.959(18) 2.8552(14) 165.8(15) 2_556

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
C1 N1 B1 O1 179.38(10) . . . . ?
C3 C2 C1 N1 88.08(15) . . . . ?
C7 C2 C1 N1 -85.87(15) . . . . ?
C8 B1 N1 C1 -61.81(14) . . . . ?
C8 B1 C14 C15 52.70(15) . . . . ?
C8 B1 C14 C19 -121.84(12) . . . . ?
C9 C8 B1 O1 77.93(15) . . . . ?
C9 C8 B1 N1 -33.78(16) . . . . ?
C13 C8 B1 O1 -95.80(13) . . . . ?
C13 C8 B1 N1 152.50(11) . . . . ?
C14 B1 N1 C1 62.85(14) . . . . ?
C14 B1 C8 C9 -157.48(12) . . . . ?
C14 B1 C8 C13 28.80(16) . . . . ?
C15 C14 B1 O1 178.60(11) . . . . ?
C15 C14 B1 N1 -70.39(14) . . . . ?
C19 C14 B1 O1 4.07(15) . . . . ?
C19 C14 B1 N1 115.07(12) . . . . ?
B1 N1 C1 C2 169.50(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, DCM'
####################################################################### 
# 
# 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_5c_15srv050
_database_code_depnum_ccdc_archive 'CCDC 1551618'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2015-02-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 Bis-(phenyl)borinic acid benzylaminobenzoate  
;
_chemical_formula_moiety         'C H2 Cl2, C26 H24 B N O2'
_chemical_formula_sum            'C27 H26 B Cl2 N O2'
_chemical_formula_weight         478.20
_chemical_melting_point          380.7(5)
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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.1158(3)
_cell_length_b                   8.9604(2)
_cell_length_c                   18.8756(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.0788(17)
_cell_angle_gamma                90.00
_cell_volume                     2387.44(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.16
_cell_measurement_theta_min      2.52
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1203 before and 0.0541 after correction.
The Ratio of minimum to maximum transmission is 0.9141.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35929
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.52
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                4421
_reflns_number_total             6345
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         6345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0400P)²+1.3200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1105
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.66909(4) 0.30124(7) 0.24053(3) 0.03273(14) Uani 1 d . . .
Cl2 Cl 0.72713(4) 0.51359(6) 0.13138(3) 0.03576(15) Uani 1 d . . .
C1S C 0.63097(15) 0.4344(3) 0.17770(13) 0.0300(5) Uani 1 d . . .
H1SA H 0.5903(16) 0.377(3) 0.1450(12) 0.033(6) Uiso 1 d . . .
H1SB H 0.6013(17) 0.514(3) 0.2022(13) 0.042(7) Uiso 1 d . . .
O1 O 0.32007(8) 0.67943(13) 0.10343(6) 0.0125(3) Uani 1 d . . .
O2 O 0.24982(8) 0.84930(13) 0.17254(6) 0.0156(3) Uani 1 d . . .
N1 N 0.24625(10) 0.54138(18) 0.20547(8) 0.0127(3) Uani 1 d . . .
C1 C 0.16802(12) 0.4575(2) 0.16815(10) 0.0162(4) Uani 1 d . . .
C2 C 0.11225(12) 0.5544(2) 0.11841(9) 0.0153(4) Uani 1 d . . .
C3 C 0.13372(13) 0.5599(2) 0.04652(10) 0.0205(4) Uani 1 d . . .
C4 C 0.08373(14) 0.6521(3) 0.00160(11) 0.0274(5) Uani 1 d . . .
C5 C 0.01213(14) 0.7412(3) 0.02764(11) 0.0291(5) Uani 1 d . . .
C6 C -0.01075(14) 0.7358(2) 0.09855(11) 0.0262(5) Uani 1 d . . .
C7 C 0.03867(13) 0.6419(2) 0.14360(10) 0.0196(4) Uani 1 d . . .
C8 C 0.27920(11) 0.80850(19) 0.11436(9) 0.0119(3) Uani 1 d . . .
C9 C 0.26956(11) 0.90224(19) 0.04982(9) 0.0126(3) Uani 1 d . . .
C10 C 0.29690(13) 0.8492(2) -0.01619(10) 0.0196(4) Uani 1 d . . .
C11 C 0.28767(15) 0.9387(2) -0.07553(11) 0.0263(5) Uani 1 d . . .
C12 C 0.25238(14) 1.0815(2) -0.06926(11) 0.0241(4) Uani 1 d . . .
C13 C 0.22500(14) 1.1354(2) -0.00385(11) 0.0221(4) Uani 1 d . . .
C14 C 0.23299(13) 1.0461(2) 0.05569(10) 0.0174(4) Uani 1 d . . .
C15 C 0.38199(11) 0.42073(19) 0.12910(9) 0.0120(3) Uani 1 d . . .
C16 C 0.39709(12) 0.2950(2) 0.17180(10) 0.0156(4) Uani 1 d . . .
C17 C 0.43663(13) 0.1647(2) 0.14588(10) 0.0187(4) Uani 1 d . . .
C18 C 0.46383(13) 0.1566(2) 0.07560(11) 0.0213(4) Uani 1 d . . .
C19 C 0.45023(14) 0.2785(2) 0.03204(11) 0.0225(4) Uani 1 d . . .
C20 C 0.40935(13) 0.4083(2) 0.05829(9) 0.0168(4) Uani 1 d . . .
C21 C 0.42107(11) 0.64568(19) 0.21580(9) 0.0126(3) Uani 1 d . . .
C22 C 0.43871(13) 0.5906(2) 0.28402(9) 0.0157(4) Uani 1 d . . .
C23 C 0.51265(13) 0.6446(2) 0.32557(10) 0.0208(4) Uani 1 d . . .
C24 C 0.57161(13) 0.7548(2) 0.29995(10) 0.0227(4) Uani 1 d . . .
C25 C 0.55618(13) 0.8120(2) 0.23256(10) 0.0198(4) Uani 1 d . . .
C26 C 0.48228(12) 0.7576(2) 0.19156(10) 0.0153(4) Uani 1 d . . .
B1 B 0.34338(13) 0.5738(2) 0.16289(10) 0.0116(4) Uani 1 d . . .
H1A H 0.2241(14) 0.630(2) 0.2178(10) 0.017(5) Uiso 1 d . . .
H1B H 0.2586(15) 0.490(2) 0.2446(12) 0.027(6) Uiso 1 d . . .
H1C H 0.1278(13) 0.417(2) 0.2051(10) 0.012(5) Uiso 1 d . . .
H1D H 0.1975(13) 0.376(2) 0.1425(10) 0.015(5) Uiso 1 d . . .
H3 H 0.1845(15) 0.500(2) 0.0285(11) 0.027(6) Uiso 1 d . . .
H4 H 0.0999(14) 0.654(2) -0.0473(12) 0.026(6) Uiso 1 d . . .
H5 H -0.0212(15) 0.804(3) -0.0033(12) 0.030(6) Uiso 1 d . . .
H6 H -0.0604(17) 0.795(3) 0.1148(12) 0.040(7) Uiso 1 d . . .
H7 H 0.0216(14) 0.638(2) 0.1921(11) 0.022(5) Uiso 1 d . . .
H10 H 0.3204(13) 0.753(2) -0.0195(10) 0.014(5) Uiso 1 d . . .
H11 H 0.3034(16) 0.901(3) -0.1212(13) 0.039(7) Uiso 1 d . . .
H12 H 0.2484(15) 1.143(3) -0.1110(12) 0.034(6) Uiso 1 d . . .
H13 H 0.2016(14) 1.238(3) -0.0002(11) 0.025(6) Uiso 1 d . . .
H14 H 0.2127(14) 1.082(2) 0.1003(11) 0.022(5) Uiso 1 d . . .
H16 H 0.3808(14) 0.299(2) 0.2208(11) 0.018(5) Uiso 1 d . . .
H17 H 0.4445(14) 0.079(2) 0.1763(11) 0.021(5) Uiso 1 d . . .
H18 H 0.4918(15) 0.067(3) 0.0571(11) 0.030(6) Uiso 1 d . . .
H19 H 0.4696(15) 0.277(2) -0.0163(12) 0.027(6) Uiso 1 d . . .
H20 H 0.4023(13) 0.495(2) 0.0284(10) 0.013(5) Uiso 1 d . . .
H22 H 0.4002(14) 0.512(2) 0.3025(11) 0.021(5) Uiso 1 d . . .
H23 H 0.5228(15) 0.605(3) 0.3722(12) 0.031(6) Uiso 1 d . . .
H24 H 0.6218(15) 0.793(2) 0.3284(11) 0.026(6) Uiso 1 d . . .
H25 H 0.5968(14) 0.889(2) 0.2149(10) 0.021(5) Uiso 1 d . . .
H26 H 0.4731(13) 0.797(2) 0.1466(10) 0.014(5) Uiso 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
Cl1 C1S 1.766(2) . ?
Cl2 C1S 1.765(2) . ?
C1S H1SA 0.99(2) . ?
C1S H1SB 0.95(3) . ?
O1 C8 1.309(2) . ?
O1 B1 1.504(2) . ?
O2 C8 1.230(2) . ?
N1 C1 1.509(2) . ?
N1 B1 1.617(2) . ?
N1 H1A 0.89(2) . ?
N1 H1B 0.89(2) . ?
C1 C2 1.501(3) . ?
C1 H1C 0.971(19) . ?
C1 H1D 0.97(2) . ?
C2 C3 1.392(3) . ?
C2 C7 1.386(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.96(2) . ?
C4 C5 1.379(3) . ?
C4 H4 0.95(2) . ?
C5 C6 1.378(3) . ?
C5 H5 0.94(2) . ?
C6 C7 1.384(3) . ?
C6 H6 0.93(2) . ?
C7 H7 0.95(2) . ?
C8 C9 1.486(2) . ?
C9 C10 1.389(2) . ?
C9 C14 1.393(2) . ?
C10 C11 1.384(3) . ?
C10 H10 0.93(2) . ?
C11 C12 1.378(3) . ?
C11 H11 0.95(2) . ?
C12 C13 1.381(3) . ?
C12 H12 0.97(2) . ?
C13 C14 1.384(3) . ?
C13 H13 0.98(2) . ?
C14 H14 0.95(2) . ?
C15 C16 1.402(2) . ?
C15 C20 1.396(2) . ?
C15 B1 1.608(3) . ?
C16 C17 1.384(3) . ?
C16 H16 0.95(2) . ?
C17 C18 1.383(3) . ?
C17 H17 0.97(2) . ?
C18 C19 1.381(3) . ?
C18 H18 0.96(2) . ?
C19 C20 1.390(3) . ?
C19 H19 0.95(2) . ?
C20 H20 0.966(19) . ?
C21 C22 1.401(2) . ?
C21 C26 1.401(2) . ?
C21 B1 1.616(3) . ?
C22 C23 1.392(3) . ?
C22 H22 0.96(2) . ?
C23 C24 1.379(3) . ?
C23 H23 0.96(2) . ?
C24 C25 1.389(3) . ?
C24 H24 0.95(2) . ?
C25 C26 1.387(3) . ?
C25 H25 0.96(2) . ?
C26 H26 0.929(19) . ?

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
Cl1 C1S H1SA 104.2(13) . . ?
Cl1 C1S H1SB 108.3(15) . . ?
Cl2 C1S Cl1 111.76(12) . . ?
Cl2 C1S H1SA 110.2(13) . . ?
Cl2 C1S H1SB 106.4(15) . . ?
H1SA C1S H1SB 116(2) . . ?
C8 O1 B1 122.30(13) . . ?
C1 N1 B1 118.55(14) . . ?
C1 N1 H1A 108.2(13) . . ?
C1 N1 H1B 106.0(14) . . ?
B1 N1 H1A 105.6(13) . . ?
B1 N1 H1B 109.9(14) . . ?
H1A N1 H1B 108.3(19) . . ?
N1 C1 H1C 106.2(11) . . ?
N1 C1 H1D 107.0(11) . . ?
C2 C1 N1 112.74(15) . . ?
C2 C1 H1C 111.0(11) . . ?
C2 C1 H1D 110.4(11) . . ?
H1C C1 H1D 109.3(16) . . ?
C3 C2 C1 121.02(17) . . ?
C7 C2 C1 120.35(17) . . ?
C7 C2 C3 118.63(17) . . ?
C2 C3 H3 119.4(13) . . ?
C4 C3 C2 120.60(19) . . ?
C4 C3 H3 119.9(13) . . ?
C3 C4 C5 120.18(19) . . ?
C3 C4 H4 118.9(13) . . ?
C5 C4 H4 120.9(13) . . ?
C4 C5 H5 119.5(14) . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.5(14) . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 118.5(15) . . ?
C7 C6 H6 121.6(15) . . ?
C2 C7 H7 120.3(12) . . ?
C6 C7 C2 120.70(18) . . ?
C6 C7 H7 119.0(12) . . ?
O1 C8 C9 114.21(14) . . ?
O2 C8 O1 123.55(15) . . ?
O2 C8 C9 122.23(15) . . ?
C10 C9 C8 121.14(16) . . ?
C10 C9 C14 119.43(16) . . ?
C14 C9 C8 119.43(15) . . ?
C9 C10 H10 118.6(12) . . ?
C11 C10 C9 120.14(18) . . ?
C11 C10 H10 121.3(12) . . ?
C10 C11 H11 120.2(15) . . ?
C12 C11 C10 120.15(19) . . ?
C12 C11 H11 119.6(14) . . ?
C11 C12 C13 120.18(18) . . ?
C11 C12 H12 119.0(14) . . ?
C13 C12 H12 120.8(14) . . ?
C12 C13 C14 120.08(18) . . ?
C12 C13 H13 119.0(12) . . ?
C14 C13 H13 120.9(12) . . ?
C9 C14 H14 119.8(13) . . ?
C13 C14 C9 120.01(17) . . ?
C13 C14 H14 120.2(13) . . ?
C16 C15 B1 120.60(15) . . ?
C20 C15 C16 116.38(16) . . ?
C20 C15 B1 122.83(16) . . ?
C15 C16 H16 119.5(12) . . ?
C17 C16 C15 122.41(17) . . ?
C17 C16 H16 118.1(12) . . ?
C16 C17 H17 120.5(12) . . ?
C18 C17 C16 119.74(18) . . ?
C18 C17 H17 119.7(12) . . ?
C17 C18 H18 120.6(13) . . ?
C19 C18 C17 119.40(18) . . ?
C19 C18 H18 120.0(13) . . ?
C18 C19 C20 120.48(18) . . ?
C18 C19 H19 121.0(13) . . ?
C20 C19 H19 118.5(13) . . ?
C15 C20 H20 117.8(11) . . ?
C19 C20 C15 121.58(18) . . ?
C19 C20 H20 120.5(11) . . ?
C22 C21 B1 123.17(15) . . ?
C26 C21 C22 116.32(16) . . ?
C26 C21 B1 120.11(15) . . ?
C21 C22 H22 119.6(12) . . ?
C23 C22 C21 121.85(17) . . ?
C23 C22 H22 118.5(12) . . ?
C22 C23 H23 119.8(13) . . ?
C24 C23 C22 120.26(18) . . ?
C24 C23 H23 119.9(13) . . ?
C23 C24 C25 119.45(18) . . ?
C23 C24 H24 120.5(13) . . ?
C25 C24 H24 120.0(13) . . ?
C24 C25 H25 119.5(12) . . ?
C26 C25 C24 119.89(18) . . ?
C26 C25 H25 120.6(12) . . ?
C21 C26 H26 119.1(12) . . ?
C25 C26 C21 122.23(18) . . ?
C25 C26 H26 118.7(12) . . ?
O1 B1 N1 107.41(13) . . ?
O1 B1 C15 108.34(13) . . ?
O1 B1 C21 110.98(14) . . ?
C15 B1 N1 109.39(14) . . ?
C15 B1 C21 110.79(14) . . ?
C21 B1 N1 109.86(13) . . ?

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
N1 H1A O2 0.89(2) 2.17(2) 2.829(2) 130.5(17) .
N1 H1B O2 0.89(2) 2.01(2) 2.875(2) 164(2) 2_545

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
C1 N1 B1 O1 66.27(19) . . . . ?
C3 C2 C1 N1 95.7(2) . . . . ?
C7 C2 C1 N1 -83.6(2) . . . . ?
C8 O1 B1 N1 55.78(19) . . . . ?
C15 B1 O1 C8 173.84(13) . . . . ?
C15 B1 N1 C1 -51.1(2) . . . . ?
C15 B1 C21 C22 -75.9(2) . . . . ?
C15 B1 C21 C26 96.63(18) . . . . ?
C16 C15 B1 O1 -171.34(14) . . . . ?
C16 C15 B1 N1 -54.5(2) . . . . ?
C20 C15 B1 O1 14.0(2) . . . . ?
C20 C15 B1 N1 130.75(17) . . . . ?
C21 B1 O1 C8 -64.32(18) . . . . ?
C21 B1 N1 C1 -172.92(14) . . . . ?
C21 B1 C15 C16 66.7(2) . . . . ?
C21 B1 C15 C20 -108.00(18) . . . . ?
C22 C21 B1 O1 163.67(15) . . . . ?
C22 C21 B1 N1 45.0(2) . . . . ?
C26 C21 B1 O1 -23.8(2) . . . . ?
C26 C21 B1 N1 -142.39(16) . . . . ?
B1 N1 C1 C2 -78.95(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


#===END 
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_5a_14srv256
_database_code_depnum_ccdc_archive 'CCDC 1551616'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2014-11-27
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.11.25 svn.r3098 for OlexSys, GUI svn.r4951)
;

_chemical_name_common            ?
_chemical_name_systematic        
; Bis(3,4,5-trifluorophenyl)-borinic acid benzylamine-4'-phenylbutanoate 
;
_chemical_formula_moiety         'C29 H24 B F6 N O2'
_chemical_formula_sum            'C29 H24 B F6 N O2'
_chemical_formula_weight         543.30
_chemical_melting_point          435.7(5)
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0140(3)
_cell_length_b                   11.7859(4)
_cell_length_c                   23.0748(7)
_cell_angle_alpha                103.8183(8)
_cell_angle_beta                 98.0649(10)
_cell_angle_gamma                96.9376(9)
_cell_volume                     2584.47(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    120
_cell_measurement_theta_max      75.22
_cell_measurement_theta_min      3.90
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.806
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_T_max  0.8688
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1135 before and 0.0890 after correction.
The Ratio of minimum to maximum transmission is 0.8195.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 1.00 1.00 0.1010
2.00 -1.00 -1.00 0.1120
-1.00 1.00 -1.00 0.1020
0.00 0.00 1.00 0.0800
0.00 0.00 -1.00 0.0980
-2.00 0.00 1.00 0.0850
2.00 0.00 -1.00 0.1060
0.00 -2.00 -1.00 0.0700
0.00 2.00 1.00 0.0720
0.00 -1.00 3.00 0.0770
0.00 1.00 -3.00 0.0970
-2.00 -1.00 3.00 0.0940
1.00 3.00 -3.00 0.1040

_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.145
_exptl_special_details           
;
The data collection nominally covered full sphere of reciprocal 
space, by a combination of 9 runs of narrow-frame ω-scans (scan 
width 0.5° ω, 10s exposure for low, 20s  for medium and 30s for 
high θ), every run at a different 2θ and/or φ angle. 
Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21248
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        65.997
_diffrn_reflns_theta_max         65.997
_diffrn_reflns_theta_min         3.905
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7740
_reflns_number_total             8496
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     719
_refine_ls_number_reflns         8496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.035
_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)+(0.1070P)²+0.4700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1626
_refine_special_details          
'Amino H atoms - refall, other H - constr (riding)'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C23(H23A,H23B), C2'(H2A',H2B'),
 C3'(H3A',H3B'), C4'(H4A',H4B'), C23'(H1,H2)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C16(H16), C18(H18),
 C22(H22), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C6'(H6'), C7'(H7'),
  C8'(H8'), C9'(H9'), C10'(H10'), C12'(H12'), C16'(H16'), C18'(H18'),
 C22'(H22'), C25'(H25'), C26'(H26'), C27'(H27'), C28'(H28'), C29'(H29')
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.24480(17) 0.48823(12) 0.50597(6) 0.0719(4) Uani 1 1 d . . . . .
F2 F 0.13628(13) 0.66036(13) 0.57276(5) 0.0624(4) Uani 1 1 d . . . . .
F3 F 0.16138(13) 0.87693(13) 0.55169(6) 0.0631(4) Uani 1 1 d . . . . .
F4 F 0.88829(12) 0.79527(12) 0.49135(5) 0.0580(3) Uani 1 1 d . . . . .
F5 F 0.94716(11) 0.60683(11) 0.41157(5) 0.0505(3) Uani 1 1 d . . . . .
F6 F 0.75337(11) 0.48118(9) 0.31670(5) 0.0442(3) Uani 1 1 d . . . . .
O1 O 0.42524(12) 0.87920(10) 0.38758(5) 0.0346(3) Uani 1 1 d . . . . .
O2 O 0.51916(13) 0.88720(11) 0.30581(5) 0.0393(3) Uani 1 1 d . . . . .
N N 0.32194(14) 0.67931(13) 0.31720(6) 0.0301(3) Uani 1 1 d . . . . .
HA H 0.369(2) 0.6723(18) 0.2860(10) 0.039(5) Uiso 1 1 d . . . . .
HB H 0.3000(19) 0.6062(18) 0.3178(8) 0.028(5) Uiso 1 1 d . . . . .
C1 C 0.47792(17) 0.93574(15) 0.35088(7) 0.0323(4) Uani 1 1 d . . . . .
C2 C 0.47587(18) 1.06655(15) 0.37177(8) 0.0350(4) Uani 1 1 d . . . . .
H2A H 0.5247 1.0959 0.4142 0.042 Uiso 1 1 calc R . . . .
H2B H 0.3798 1.0791 0.3715 0.042 Uiso 1 1 calc R . . . .
C3 C 0.54008(19) 1.13984(15) 0.33378(8) 0.0383(4) Uani 1 1 d . . . . .
H3A H 0.4955 1.1080 0.2908 0.046 Uiso 1 1 calc R . . . .
H3B H 0.6381 1.1326 0.3364 0.046 Uiso 1 1 calc R . . . .
C4 C 0.52644(19) 1.27141(15) 0.35462(9) 0.0409(4) Uani 1 1 d . . . . .
H4A H 0.5623 1.3007 0.3986 0.049 Uiso 1 1 calc R . . . .
H4B H 0.5835 1.3169 0.3335 0.049 Uiso 1 1 calc R . . . .
C5 C 0.38198(19) 1.29458(14) 0.34266(8) 0.0373(4) Uani 1 1 d . . . . .
C6 C 0.2979(2) 1.29907(16) 0.38621(9) 0.0421(4) Uani 1 1 d . . . . .
H6 H 0.3330 1.2896 0.4249 0.051 Uiso 1 1 calc R . . . .
C7 C 0.1636(2) 1.31720(17) 0.37380(10) 0.0500(5) Uani 1 1 d . . . . .
H7 H 0.1074 1.3193 0.4038 0.060 Uiso 1 1 calc R . . . .
C8 C 0.1112(2) 1.33228(18) 0.31793(11) 0.0550(5) Uani 1 1 d . . . . .
H8 H 0.0194 1.3451 0.3096 0.066 Uiso 1 1 calc R . . . .
C9 C 0.1935(2) 1.32864(19) 0.27425(10) 0.0533(5) Uani 1 1 d . . . . .
H9 H 0.1582 1.3390 0.2358 0.064 Uiso 1 1 calc R . . . .
C10 C 0.3270(2) 1.30988(17) 0.28659(9) 0.0453(4) Uani 1 1 d . . . . .
H10 H 0.3824 1.3074 0.2562 0.054 Uiso 1 1 calc R . . . .
C11 C 0.33476(17) 0.72506(15) 0.43491(7) 0.0334(4) Uani 1 1 d . . . . .
C12 C 0.3228(2) 0.61441(17) 0.44727(8) 0.0412(4) Uani 1 1 d . . . . .
H12 H 0.3618 0.5528 0.4243 0.049 Uiso 1 1 calc R . . . .
C13 C 0.2543(2) 0.59399(18) 0.49275(9) 0.0465(5) Uani 1 1 d . . . . .
C14 C 0.19805(19) 0.68109(19) 0.52737(8) 0.0447(5) Uani 1 1 d . . . . .
C15 C 0.21139(19) 0.79007(19) 0.51592(8) 0.0449(5) Uani 1 1 d . . . . .
C16 C 0.27714(18) 0.81270(17) 0.47010(8) 0.0389(4) Uani 1 1 d . . . . .
H16 H 0.2830 0.8888 0.4626 0.047 Uiso 1 1 calc R . . . .
C17 C 0.56258(17) 0.70636(14) 0.38679(7) 0.0317(4) Uani 1 1 d . . . . .
C18 C 0.66460(19) 0.76898(16) 0.43595(8) 0.0385(4) Uani 1 1 d . . . . .
H18 H 0.6463 0.8360 0.4641 0.046 Uiso 1 1 calc R . . . .
C19 C 0.79074(19) 0.73448(18) 0.44390(8) 0.0410(4) Uani 1 1 d . . . . .
C20 C 0.82270(18) 0.63843(17) 0.40381(8) 0.0392(4) Uani 1 1 d . . . . .
C21 C 0.72280(18) 0.57576(15) 0.35598(8) 0.0357(4) Uani 1 1 d . . . . .
C22 C 0.59478(17) 0.60781(15) 0.34693(8) 0.0329(4) Uani 1 1 d . . . . .
H22 H 0.5280 0.5626 0.3134 0.040 Uiso 1 1 calc R . . . .
C23 C 0.19275(18) 0.72610(15) 0.30034(8) 0.0370(4) Uani 1 1 d . . . . .
H23A H 0.2162 0.8053 0.2935 0.044 Uiso 1 1 calc R . . . .
H23B H 0.1409 0.7347 0.3342 0.044 Uiso 1 1 calc R . . . .
C24 C 0.10486(17) 0.64444(15) 0.24392(8) 0.0326(4) Uani 1 1 d . . . . .
C25 C 0.00726(17) 0.55469(16) 0.24873(8) 0.0368(4) Uani 1 1 d . . . . .
H25 H -0.0074 0.5480 0.2877 0.044 Uiso 1 1 calc R . . . .
C26 C -0.06926(18) 0.47450(16) 0.19719(9) 0.0418(4) Uani 1 1 d . . . . .
H26 H -0.1345 0.4122 0.2009 0.050 Uiso 1 1 calc R . . . .
C27 C -0.05032(19) 0.48559(16) 0.14045(9) 0.0413(4) Uani 1 1 d . . . . .
H27 H -0.1025 0.4307 0.1051 0.050 Uiso 1 1 calc R . . . .
C28 C 0.04457(19) 0.57657(16) 0.13511(8) 0.0395(4) Uani 1 1 d . . . . .
H28 H 0.0564 0.5848 0.0961 0.047 Uiso 1 1 calc R . . . .
C29 C 0.12240(17) 0.65564(15) 0.18658(8) 0.0356(4) Uani 1 1 d . . . . .
H29 H 0.1879 0.7176 0.1827 0.043 Uiso 1 1 calc R . . . .
B B 0.4153(2) 0.74968(17) 0.38166(8) 0.0327(4) Uani 1 1 d . . . . .
F1' F 0.25138(12) 1.05041(10) 0.18245(5) 0.0503(3) Uani 1 1 d . . . . .
F2' F 0.05822(11) 0.93009(11) 0.08607(5) 0.0488(3) Uani 1 1 d . . . . .
F3' F 0.10530(11) 0.72983(11) 0.01147(5) 0.0518(3) Uani 1 1 d . . . . .
F4' F 0.84299(12) 0.57361(11) -0.02138(5) 0.0534(3) Uani 1 1 d . . . . .
F5' F 0.86203(12) 0.76710(12) -0.06564(5) 0.0548(3) Uani 1 1 d . . . . .
F6' F 0.74532(13) 0.95345(11) -0.01713(5) 0.0559(3) Uani 1 1 d . . . . .
O1' O 0.53163(12) 0.62123(10) 0.12675(5) 0.0317(3) Uani 1 1 d . . . . .
O2' O 0.45189(13) 0.65056(11) 0.21362(5) 0.0386(3) Uani 1 1 d . . . . .
N' N 0.65802(15) 0.81929(12) 0.19345(6) 0.0305(3) Uani 1 1 d . . . . .
HA' H 0.688(2) 0.8945(19) 0.1938(8) 0.032(5) Uiso 1 1 d . . . . .
HB' H 0.610(2) 0.8256(19) 0.2225(10) 0.043(6) Uiso 1 1 d . . . . .
C1' C 0.46783(16) 0.58439(15) 0.16691(7) 0.0322(4) Uani 1 1 d . . . . .
C2' C 0.42329(17) 0.45254(15) 0.14947(8) 0.0366(4) Uani 1 1 d . . . . .
H2A' H 0.3766 0.4261 0.1066 0.044 Uiso 1 1 calc R . . . .
H2B' H 0.3579 0.4314 0.1751 0.044 Uiso 1 1 calc R . . . .
C3' C 0.54762(17) 0.39042(15) 0.15774(8) 0.0359(4) Uani 1 1 d . . . . .
H3A' H 0.5865 0.4098 0.2015 0.043 Uiso 1 1 calc R . . . .
H3B' H 0.6181 0.4216 0.1370 0.043 Uiso 1 1 calc R . . . .
C4' C 0.51494(18) 0.25568(15) 0.13304(9) 0.0387(4) Uani 1 1 d . . . . .
H4A' H 0.4447 0.2233 0.1536 0.046 Uiso 1 1 calc R . . . .
H4B' H 0.4780 0.2351 0.0891 0.046 Uiso 1 1 calc R . . . .
C5' C 0.64255(18) 0.20201(14) 0.14367(8) 0.0356(4) Uani 1 1 d . . . . .
C6' C 0.68498(19) 0.17887(15) 0.19920(8) 0.0396(4) Uani 1 1 d . . . . .
H6' H 0.6282 0.1895 0.2292 0.048 Uiso 1 1 calc R . . . .
C7' C 0.8089(2) 0.14051(17) 0.21138(9) 0.0452(4) Uani 1 1 d . . . . .
H7' H 0.8364 0.1248 0.2494 0.054 Uiso 1 1 calc R . . . .
C8' C 0.8928(2) 0.12499(17) 0.16800(10) 0.0458(5) Uani 1 1 d . . . . .
H8' H 0.9785 0.1000 0.1765 0.055 Uiso 1 1 calc R . . . .
C9' C 0.8510(2) 0.14611(17) 0.11245(9) 0.0451(4) Uani 1 1 d . . . . .
H9' H 0.9076 0.1346 0.0824 0.054 Uiso 1 1 calc R . . . .
C10' C 0.72668(19) 0.18405(15) 0.10029(8) 0.0397(4) Uani 1 1 d . . . . .
H10' H 0.6987 0.1979 0.0619 0.048 Uiso 1 1 calc R . . . .
C11' C 0.42469(17) 0.80547(14) 0.12044(7) 0.0308(3) Uani 1 1 d . . . . .
C12' C 0.39825(17) 0.90919(15) 0.15796(8) 0.0336(4) Uani 1 1 d . . . . .
H12' H 0.4647 0.9521 0.1922 0.040 Uiso 1 1 calc R . . . .
C13' C 0.27635(19) 0.94999(15) 0.14580(8) 0.0371(4) Uani 1 1 d . . . . .
C14' C 0.17710(17) 0.89036(16) 0.09712(8) 0.0374(4) Uani 1 1 d . . . . .
C15' C 0.20266(18) 0.78802(17) 0.05955(8) 0.0371(4) Uani 1 1 d . . . . .
C16' C 0.32326(18) 0.74580(16) 0.07051(8) 0.0347(4) Uani 1 1 d . . . . .
H16' H 0.3381 0.6752 0.0439 0.042 Uiso 1 1 calc R . . . .
C17' C 0.65076(16) 0.75638(15) 0.07555(7) 0.0318(4) Uani 1 1 d . . . . .
C18' C 0.71362(18) 0.66176(16) 0.05038(8) 0.0361(4) Uani 1 1 d . . . . .
H18' H 0.7069 0.5931 0.0653 0.043 Uiso 1 1 calc R . . . .
C19' C 0.78553(18) 0.66684(17) 0.00403(8) 0.0408(4) Uani 1 1 d . . . . .
C20' C 0.79696(18) 0.76502(18) -0.01864(8) 0.0417(4) Uani 1 1 d . . . . .
C21' C 0.73641(19) 0.85938(17) 0.00653(8) 0.0406(4) Uani 1 1 d . . . . .
C22' C 0.66387(18) 0.85660(16) 0.05291(8) 0.0365(4) Uani 1 1 d . . . . .
H22' H 0.6228 0.9227 0.0695 0.044 Uiso 1 1 calc R . . . .
C23' C 0.78103(18) 0.76519(15) 0.21119(8) 0.0367(4) Uani 1 1 d . . . . .
H1 H 0.7510 0.6924 0.2233 0.044 Uiso 1 1 calc R . . . .
H2 H 0.8268 0.7426 0.1757 0.044 Uiso 1 1 calc R . . . .
C24' C 0.88117(17) 0.84908(14) 0.26265(8) 0.0326(4) Uani 1 1 d . . . . .
C25' C 0.86600(18) 0.85692(15) 0.32227(8) 0.0359(4) Uani 1 1 d . . . . .
H25' H 0.7923 0.8083 0.3307 0.043 Uiso 1 1 calc R . . . .
C26' C 0.9580(2) 0.93541(16) 0.36966(8) 0.0395(4) Uani 1 1 d . . . . .
H26' H 0.9484 0.9390 0.4104 0.047 Uiso 1 1 calc R . . . .
C27' C 1.06382(19) 1.00859(16) 0.35752(8) 0.0398(4) Uani 1 1 d . . . . .
H27' H 1.1259 1.0630 0.3900 0.048 Uiso 1 1 calc R . . . .
C28' C 1.07919(18) 1.00251(16) 0.29813(8) 0.0392(4) Uani 1 1 d . . . . .
H28' H 1.1509 1.0534 0.2898 0.047 Uiso 1 1 calc R . . . .
C29' C 0.98920(18) 0.92161(15) 0.25097(8) 0.0357(4) Uani 1 1 d . . . . .
H29' H 1.0014 0.9156 0.2103 0.043 Uiso 1 1 calc R . . . .
B' B 0.56349(19) 0.75015(16) 0.12903(8) 0.0307(4) 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 C13 1.348(2) . ?
F2 C14 1.344(2) . ?
F3 C15 1.348(2) . ?
F4 C19 1.350(2) . ?
F5 C20 1.344(2) . ?
F6 C21 1.355(2) . ?
O1 C1 1.323(2) . ?
O1 B 1.490(2) . ?
O2 C1 1.214(2) . ?
N C23 1.504(2) . ?
N B 1.615(2) . ?
C1 C2 1.505(2) . ?
C2 C3 1.521(2) . ?
C3 C4 1.539(2) . ?
C4 C5 1.504(3) . ?
C5 C6 1.394(3) . ?
C5 C10 1.395(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.385(3) . ?
C9 C10 1.382(3) . ?
C11 C12 1.395(3) . ?
C11 C16 1.391(2) . ?
C11 B 1.623(2) . ?
C12 C13 1.383(3) . ?
C13 C14 1.372(3) . ?
C14 C15 1.367(3) . ?
C15 C16 1.382(3) . ?
C17 C18 1.403(2) . ?
C17 C22 1.401(2) . ?
C17 B 1.616(3) . ?
C18 C19 1.374(3) . ?
C19 C20 1.382(3) . ?
C20 C21 1.374(3) . ?
C21 C22 1.382(2) . ?
C23 C24 1.507(2) . ?
C24 C25 1.387(2) . ?
C24 C29 1.394(2) . ?
C25 C26 1.388(3) . ?
C26 C27 1.383(3) . ?
C27 C28 1.385(3) . ?
C28 C29 1.387(3) . ?
F1' C13' 1.353(2) . ?
F2' C14' 1.345(2) . ?
F3' C15' 1.350(2) . ?
F4' C19' 1.350(2) . ?
F5' C20' 1.345(2) . ?
F6' C21' 1.347(2) . ?
O1' C1' 1.322(2) . ?
O1' B' 1.501(2) . ?
O2' C1' 1.213(2) . ?
N' C23' 1.505(2) . ?
N' B' 1.616(2) . ?
C1' C2' 1.503(2) . ?
C2' C3' 1.531(2) . ?
C3' C4' 1.531(2) . ?
C4' C5' 1.508(2) . ?
C5' C6' 1.392(3) . ?
C5' C10' 1.391(3) . ?
C6' C7' 1.386(3) . ?
C7' C8' 1.389(3) . ?
C8' C9' 1.381(3) . ?
C9' C10' 1.387(3) . ?
C11' C12' 1.397(2) . ?
C11' C16' 1.402(2) . ?
C11' B' 1.612(2) . ?
C12' C13' 1.382(2) . ?
C13' C14' 1.373(3) . ?
C14' C15' 1.382(3) . ?
C15' C16' 1.375(2) . ?
C17' C18' 1.393(2) . ?
C17' C22' 1.401(2) . ?
C17' B' 1.619(2) . ?
C18' C19' 1.379(3) . ?
C19' C20' 1.378(3) . ?
C20' C21' 1.377(3) . ?
C21' C22' 1.380(3) . ?
C23' C24' 1.503(2) . ?
C24' C25' 1.388(2) . ?
C24' C29' 1.394(2) . ?
C25' C26' 1.389(3) . ?
C26' C27' 1.387(3) . ?
C27' C28' 1.386(3) . ?
C28' C29' 1.388(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
C1 O1 B 125.27(13) . . ?
C23 N B 115.90(13) . . ?
O1 C1 C2 110.86(14) . . ?
O2 C1 O1 123.95(15) . . ?
O2 C1 C2 125.18(15) . . ?
C1 C2 C3 114.68(14) . . ?
C2 C3 C4 112.32(15) . . ?
C5 C4 C3 113.61(15) . . ?
C6 C5 C4 121.67(17) . . ?
C6 C5 C10 117.81(18) . . ?
C10 C5 C4 120.50(17) . . ?
C7 C6 C5 120.90(19) . . ?
C8 C7 C6 120.3(2) . . ?
C7 C8 C9 119.55(19) . . ?
C10 C9 C8 120.0(2) . . ?
C9 C10 C5 121.38(19) . . ?
C12 C11 B 120.50(15) . . ?
C16 C11 C12 117.75(16) . . ?
C16 C11 B 121.74(16) . . ?
C13 C12 C11 120.26(18) . . ?
F1 C13 C12 120.75(18) . . ?
F1 C13 C14 117.61(17) . . ?
C14 C13 C12 121.61(18) . . ?
F2 C14 C13 120.50(19) . . ?
F2 C14 C15 121.23(19) . . ?
C15 C14 C13 118.22(17) . . ?
F3 C15 C14 118.13(17) . . ?
F3 C15 C16 120.29(19) . . ?
C14 C15 C16 121.56(18) . . ?
C15 C16 C11 120.58(18) . . ?
C18 C17 B 117.92(15) . . ?
C22 C17 C18 117.23(16) . . ?
C22 C17 B 124.80(15) . . ?
C19 C18 C17 120.77(17) . . ?
F4 C19 C18 120.36(17) . . ?
F4 C19 C20 117.91(17) . . ?
C18 C19 C20 121.72(17) . . ?
F5 C20 C19 121.11(17) . . ?
F5 C20 C21 121.04(17) . . ?
C21 C20 C19 117.85(16) . . ?
F6 C21 C20 118.10(16) . . ?
F6 C21 C22 120.09(16) . . ?
C20 C21 C22 121.80(17) . . ?
C21 C22 C17 120.60(16) . . ?
N C23 C24 111.21(13) . . ?
C25 C24 C23 119.83(16) . . ?
C25 C24 C29 119.17(16) . . ?
C29 C24 C23 120.98(16) . . ?
C24 C25 C26 120.62(17) . . ?
C27 C26 C25 119.81(17) . . ?
C26 C27 C28 120.06(17) . . ?
C27 C28 C29 120.13(17) . . ?
C28 C29 C24 120.17(16) . . ?
O1 B N 108.72(13) . . ?
O1 B C11 105.44(13) . . ?
O1 B C17 112.93(14) . . ?
N B C11 108.09(13) . . ?
N B C17 109.60(13) . . ?
C17 B C11 111.85(14) . . ?
C1' O1' B' 121.90(13) . . ?
C23' N' B' 115.39(12) . . ?
O1' C1' C2' 112.73(14) . . ?
O2' C1' O1' 122.88(15) . . ?
O2' C1' C2' 124.35(15) . . ?
C1' C2' C3' 109.89(14) . . ?
C2' C3' C4' 113.58(14) . . ?
C5' C4' C3' 109.93(14) . . ?
C6' C5' C4' 120.62(16) . . ?
C10' C5' C4' 120.78(16) . . ?
C10' C5' C6' 118.37(17) . . ?
C7' C6' C5' 120.92(17) . . ?
C6' C7' C8' 120.02(18) . . ?
C9' C8' C7' 119.59(18) . . ?
C8' C9' C10' 120.25(18) . . ?
C9' C10' C5' 120.83(18) . . ?
C12' C11' C16' 117.30(15) . . ?
C12' C11' B' 125.38(15) . . ?
C16' C11' B' 117.30(14) . . ?
C13' C12' C11' 120.64(16) . . ?
F1' C13' C12' 120.28(16) . . ?
F1' C13' C14' 118.08(16) . . ?
C14' C13' C12' 121.63(16) . . ?
F2' C14' C13' 121.17(16) . . ?
F2' C14' C15' 120.70(16) . . ?
C13' C14' C15' 118.13(16) . . ?
F3' C15' C14' 118.08(16) . . ?
F3' C15' C16' 120.54(16) . . ?
C16' C15' C14' 121.38(16) . . ?
C15' C16' C11' 120.90(16) . . ?
C18' C17' C22' 118.19(16) . . ?
C18' C17' B' 120.91(15) . . ?
C22' C17' B' 120.89(15) . . ?
C19' C18' C17' 120.56(17) . . ?
F4' C19' C18' 120.35(18) . . ?
F4' C19' C20' 118.49(16) . . ?
C20' C19' C18' 121.13(17) . . ?
F5' C20' C19' 120.73(18) . . ?
F5' C20' C21' 120.66(17) . . ?
C21' C20' C19' 118.58(16) . . ?
F6' C21' C20' 117.94(16) . . ?
F6' C21' C22' 120.55(18) . . ?
C20' C21' C22' 121.46(17) . . ?
C21' C22' C17' 120.07(17) . . ?
C24' C23' N' 111.87(13) . . ?
C25' C24' C23' 120.55(16) . . ?
C25' C24' C29' 119.15(16) . . ?
C29' C24' C23' 120.29(16) . . ?
C24' C25' C26' 120.36(16) . . ?
C27' C26' C25' 120.02(17) . . ?
C28' C27' C26' 120.15(17) . . ?
C27' C28' C29' 119.60(17) . . ?
C28' C29' C24' 120.68(16) . . ?
O1' B' N' 109.01(13) . . ?
O1' B' C11' 110.56(13) . . ?
O1' B' C17' 105.71(13) . . ?
N' B' C17' 108.86(13) . . ?
C11' B' N' 110.06(13) . . ?
C11' B' C17' 112.51(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N HA O2' 0.91(2) 1.94(2) 2.8484(19) 173.8(19) .
N' HB' O2 0.87(2) 2.25(2) 3.0961(19) 165.6(19) .

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Et2O'
####################################################################### 
# 
# 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_7a_14srv091
_database_code_depnum_ccdc_archive 'CCDC 1563948'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2017-07-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2016/6

_chemical_name_common            ?
_chemical_name_systematic        3,4,5-trifluorophenylboroxine
_chemical_formula_moiety         'C18 H6 B3 F9 O3'
_chemical_formula_sum            'C18 H6 B3 F9 O3'
_chemical_formula_weight         473.66
_chemical_melting_point          ?
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.8358(9)
_cell_length_b                   12.6583(9)
_cell_length_c                   12.8851(9)
_cell_angle_alpha                90
_cell_angle_beta                 119.060(2)
_cell_angle_gamma                90
_cell_volume                     1830.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3694
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.94
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1260 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9160.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.167
_exptl_special_details           
;
 The data collection nominally covered full sphere of reciprocal 
space, by a combination of 3 runs of narrow-frame ω-scans (scan 
width 0.5° ω, 5s exposure), every run at a different φ angle. 
Crystal to detector distance 3.50 cm. 
  Phase transition on cooling below 210 K.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9411
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.426
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1161
_reflns_number_total             1619
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.078
_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)+(0.0607P)²+0.4114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.500000 1.24681(13) 0.250000 0.0993(6) Uani 1 2 d S T P . .
F2 F 0.44405(14) 1.14143(10) 0.39628(13) 0.1033(5) Uani 1 1 d . . . . .
F3 F 0.26001(12) 0.62720(11) 0.55836(12) 0.0989(5) Uani 1 1 d . . . . .
F4 F 0.23598(10) 0.41788(11) 0.53833(11) 0.0891(5) Uani 1 1 d . . . . .
F5 F 0.30333(12) 0.31099(10) 0.40217(13) 0.0999(5) Uani 1 1 d . . . . .
O1 O 0.45189(10) 0.74477(10) 0.30832(10) 0.0607(4) Uani 1 1 d . . . . .
O2 O 0.500000 0.58253(13) 0.250000 0.0563(5) Uani 1 2 d S T P . .
C1 C 0.500000 1.1409(2) 0.250000 0.0659(7) Uani 1 2 d S T P . .
C2 C 0.47049(17) 1.08586(16) 0.32337(17) 0.0650(5) Uani 1 1 d . . . . .
C3 C 0.46848(15) 0.97819(15) 0.32341(15) 0.0603(5) Uani 1 1 d . . . . .
H3 H 0.445578 0.941606 0.373535 0.072 Uiso 1 1 calc R . . . .
C4 C 0.500000 0.9218(2) 0.250000 0.0538(6) Uani 1 2 d S T P . .
C5 C 0.38497(14) 0.57619(14) 0.36370(15) 0.0521(5) Uani 1 1 d . . . . .
C6 C 0.34678(16) 0.63052(15) 0.43310(16) 0.0609(5) Uani 1 1 d . . . . .
H6 H 0.355333 0.705098 0.440787 0.073 Uiso 1 1 calc R . . . .
C7 C 0.29705(16) 0.57683(17) 0.49015(17) 0.0638(5) Uani 1 1 d . . . . .
C8 C 0.28307(14) 0.46991(17) 0.48043(16) 0.0631(5) Uani 1 1 d . . . . .
C9 C 0.31879(16) 0.41619(15) 0.41081(18) 0.0635(5) Uani 1 1 d . . . . .
C10 C 0.36981(15) 0.46756(15) 0.35300(15) 0.0586(5) Uani 1 1 d . . . . .
H10 H 0.394707 0.428801 0.305748 0.070 Uiso 1 1 calc R . . . .
B1 B 0.500000 0.7998(2) 0.250000 0.0551(7) Uani 1 2 d S T P . .
B2 B 0.44702(17) 0.63658(17) 0.30458(17) 0.0536(5) 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 C1 1.341(3) . ?
F2 C2 1.343(2) . ?
F3 C7 1.346(2) . ?
F4 C8 1.339(2) . ?
F5 C9 1.343(2) . ?
O1 B1 1.372(2) . ?
O1 B2 1.371(2) . ?
O2 B2 1.375(2) . ?
O2 B2 1.375(2) 2_655 ?
C1 C2 1.368(2) . ?
C1 C2 1.368(2) 2_655 ?
C2 C3 1.363(3) . ?
C3 C4 1.393(2) . ?
C4 B1 1.544(4) . ?
C5 C6 1.392(2) . ?
C5 C10 1.386(2) . ?
C5 B2 1.545(3) . ?
C6 C7 1.366(2) . ?
C7 C8 1.363(3) . ?
C8 C9 1.370(3) . ?
C9 C10 1.371(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
B2 O1 B1 120.87(16) . . ?
B2 O2 B2 120.3(2) 2_655 . ?
F1 C1 C2 120.62(13) . . ?
F1 C1 C2 120.62(13) . 2_655 ?
C2 C1 C2 118.8(3) . 2_655 ?
F2 C2 C1 117.77(19) . . ?
F2 C2 C3 120.82(17) . . ?
C3 C2 C1 121.41(18) . . ?
C2 C3 C4 120.03(18) . . ?
C3 C4 C3 118.3(2) 2_655 . ?
C3 C4 B1 120.83(12) 2_655 . ?
C3 C4 B1 120.83(12) . . ?
C6 C5 B2 119.92(17) . . ?
C10 C5 C6 118.53(17) . . ?
C10 C5 B2 121.51(16) . . ?
C7 C6 C5 120.15(18) . . ?
F3 C7 C6 121.44(19) . . ?
F3 C7 C8 117.25(17) . . ?
C8 C7 C6 121.31(18) . . ?
F4 C8 C7 120.80(19) . . ?
F4 C8 C9 120.38(19) . . ?
C7 C8 C9 118.82(17) . . ?
F5 C9 C8 117.62(17) . . ?
F5 C9 C10 121.03(18) . . ?
C8 C9 C10 121.35(18) . . ?
C9 C10 C5 119.82(17) . . ?
O1 B1 O1 119.0(2) . 2_655 ?
O1 B1 C4 120.52(12) 2_655 . ?
O1 B1 C4 120.52(12) . . ?
O1 B2 O2 119.33(17) . . ?
O1 B2 C5 120.17(16) . . ?
O2 B2 C5 120.49(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# 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_11d_16srv431
_database_code_depnum_ccdc_archive 'CCDC 1551624'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2016-11-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;

_chemical_name_common            ?
_chemical_name_systematic        
'Di-2-iodophenylboronic B-O-B di-2-phenylacetate '
_chemical_formula_moiety         'C28 H22 B2 I2 O5'
_chemical_formula_sum            'C28 H22 B2 I2 O5'
_chemical_formula_weight         713.87
_chemical_melting_point          382(1)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6350(5)
_cell_length_b                   11.4814(5)
_cell_length_c                   12.2457(6)
_cell_angle_alpha                83.1389(18)
_cell_angle_beta                 87.0947(19)
_cell_angle_gamma                64.1817(17)
_cell_volume                     1336.36(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9017
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.29
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.621
_exptl_absorpt_coefficient_mu    2.390
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0629 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.8689.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21913
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.453
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6143
_reflns_number_total             7764
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         7764
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+0.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0580
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.38294(2) 0.66826(2) 0.33947(2) 0.02343(5) Uani 1 1 d . . . . .
I2 I 0.71523(2) 1.27960(2) 0.34759(2) 0.02189(5) Uani 1 1 d . . . . .
O1 O 0.98260(16) 1.05923(14) 0.18677(12) 0.0143(3) Uani 1 1 d . . . . .
O2 O 1.12063(16) 0.83051(14) 0.16755(12) 0.0165(3) Uani 1 1 d . . . . .
O3 O 0.90114(16) 0.92433(15) 0.10352(13) 0.0179(3) Uani 1 1 d . . . . .
O4 O 1.05693(16) 0.90559(15) 0.34945(12) 0.0151(3) Uani 1 1 d . . . . .
O5 O 0.83857(17) 0.96873(15) 0.29183(12) 0.0185(3) Uani 1 1 d . . . . .
C1 C 1.2432(2) 0.9550(2) 0.23752(18) 0.0151(4) Uani 1 1 d . . . . .
C2 C 1.3695(2) 0.8535(2) 0.27539(18) 0.0173(5) Uani 1 1 d . . . . .
C3 C 1.4945(3) 0.8642(2) 0.2709(2) 0.0229(5) Uani 1 1 d . . . . .
H3 H 1.5780 0.7927 0.2980 0.027 Uiso 1 1 calc R . . . .
C4 C 1.4967(3) 0.9796(3) 0.2266(2) 0.0281(6) Uani 1 1 d . . . . .
H4 H 1.5821 0.9875 0.2220 0.034 Uiso 1 1 calc R . . . .
C5 C 1.3742(3) 1.0835(3) 0.1890(2) 0.0264(6) Uani 1 1 d . . . . .
H5 H 1.3751 1.1633 0.1587 0.032 Uiso 1 1 calc R . . . .
C6 C 1.2501(3) 1.0711(2) 0.19551(19) 0.0199(5) Uani 1 1 d . . . . .
H6 H 1.1665 1.1440 0.1706 0.024 Uiso 1 1 calc R . . . .
C7 C 0.7223(2) 1.1531(2) 0.13606(18) 0.0153(4) Uani 1 1 d . . . . .
C8 C 0.6510(2) 1.2635(2) 0.19118(18) 0.0174(5) Uani 1 1 d . . . . .
C9 C 0.5301(3) 1.3681(2) 0.1499(2) 0.0253(5) Uani 1 1 d . . . . .
H9 H 0.4848 1.4419 0.1895 0.030 Uiso 1 1 calc R . . . .
C10 C 0.4761(3) 1.3644(3) 0.0510(2) 0.0270(6) Uani 1 1 d . . . . .
H10 H 0.3937 1.4358 0.0220 0.032 Uiso 1 1 calc R . . . .
C11 C 0.5418(3) 1.2566(2) -0.00576(19) 0.0228(5) Uani 1 1 d . . . . .
H11 H 0.5042 1.2534 -0.0735 0.027 Uiso 1 1 calc R . . . .
C12 C 0.6623(2) 1.1535(2) 0.03621(18) 0.0185(5) Uani 1 1 d . . . . .
H12 H 0.7063 1.0800 -0.0039 0.022 Uiso 1 1 calc R . . . .
C13 C 1.0260(2) 0.8348(2) 0.10628(18) 0.0167(5) Uani 1 1 d . . . . .
C14 C 1.0601(3) 0.7256(2) 0.03764(18) 0.0204(5) Uani 1 1 d . . . . .
H14A H 1.1606 0.6878 0.0185 0.024 Uiso 1 1 calc R . . . .
H14B H 1.0053 0.7582 -0.0314 0.024 Uiso 1 1 calc R . . . .
C15 C 1.0251(2) 0.6225(2) 0.10278(18) 0.0160(4) Uani 1 1 d . . . . .
C16 C 1.1231(3) 0.5272(2) 0.1750(2) 0.0211(5) Uani 1 1 d . . . . .
H16 H 1.2107 0.5283 0.1844 0.025 Uiso 1 1 calc R . . . .
C17 C 1.0940(3) 0.4311(2) 0.2331(2) 0.0294(6) Uani 1 1 d . . . . .
H17 H 1.1619 0.3659 0.2818 0.035 Uiso 1 1 calc R . . . .
C18 C 0.9676(3) 0.4297(3) 0.2208(2) 0.0346(7) Uani 1 1 d . . . . .
H18 H 0.9483 0.3629 0.2601 0.042 Uiso 1 1 calc R . . . .
C19 C 0.8680(3) 0.5254(3) 0.1511(2) 0.0346(7) Uani 1 1 d . . . . .
H19 H 0.7798 0.5249 0.1436 0.042 Uiso 1 1 calc R . . . .
C20 C 0.8965(3) 0.6219(3) 0.0922(2) 0.0264(6) Uani 1 1 d . . . . .
H20 H 0.8277 0.6876 0.0446 0.032 Uiso 1 1 calc R . . . .
C21 C 0.9315(2) 0.9245(2) 0.36636(18) 0.0170(5) Uani 1 1 d . . . . .
C22 C 0.8909(3) 0.8944(2) 0.48128(18) 0.0212(5) Uani 1 1 d . . . . .
H22A H 0.8324 0.9772 0.5120 0.025 Uiso 1 1 calc R . . . .
H22B H 0.9765 0.8486 0.5268 0.025 Uiso 1 1 calc R . . . .
C23 C 0.8117(2) 0.8118(2) 0.48992(18) 0.0180(5) Uani 1 1 d . . . . .
C24 C 0.8688(3) 0.6903(2) 0.4525(2) 0.0281(6) Uani 1 1 d . . . . .
H24 H 0.9569 0.6594 0.4166 0.034 Uiso 1 1 calc R . . . .
C25 C 0.7968(4) 0.6136(3) 0.4675(2) 0.0388(7) Uani 1 1 d . . . . .
H25 H 0.8353 0.5304 0.4413 0.047 Uiso 1 1 calc R . . . .
C26 C 0.6699(3) 0.6580(3) 0.5202(2) 0.0398(8) Uani 1 1 d . . . . .
H26 H 0.6219 0.6045 0.5319 0.048 Uiso 1 1 calc R . . . .
C27 C 0.6124(3) 0.7789(3) 0.5559(2) 0.0364(7) Uani 1 1 d . . . . .
H27 H 0.5241 0.8095 0.5915 0.044 Uiso 1 1 calc R . . . .
C28 C 0.6818(3) 0.8563(3) 0.5405(2) 0.0243(5) Uani 1 1 d . . . . .
H28 H 0.6407 0.9406 0.5646 0.029 Uiso 1 1 calc R . . . .
B1 B 1.0974(3) 0.9481(2) 0.2321(2) 0.0155(5) Uani 1 1 d . . . . .
B2 B 0.8650(3) 1.0351(2) 0.1776(2) 0.0166(5) 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
I1 C2 2.123(2) . ?
I2 C8 2.121(2) . ?
O1 B1 1.403(3) . ?
O1 B2 1.406(3) . ?
O2 C13 1.266(3) . ?
O2 B1 1.567(3) . ?
O3 C13 1.276(3) . ?
O3 B2 1.549(3) . ?
O4 C21 1.265(3) . ?
O4 B1 1.563(3) . ?
O5 C21 1.269(3) . ?
O5 B2 1.584(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.401(3) . ?
C1 B1 1.591(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.380(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.386(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.406(3) . ?
C7 B2 1.588(3) . ?
C8 C9 1.389(3) . ?
C9 C10 1.380(4) . ?
C10 C11 1.380(3) . ?
C11 C12 1.382(3) . ?
C13 C14 1.496(3) . ?
C14 C15 1.518(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.384(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.368(4) . ?
C18 C19 1.382(4) . ?
C19 C20 1.385(4) . ?
C21 C22 1.496(3) . ?
C22 C23 1.511(3) . ?
C23 C24 1.382(3) . ?
C23 C28 1.389(3) . ?
C24 C25 1.389(4) . ?
C25 C26 1.375(5) . ?
C26 C27 1.368(4) . ?
C27 C28 1.374(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
B1 O1 B2 111.77(18) . . ?
C13 O2 B1 121.02(18) . . ?
C13 O3 B2 117.88(18) . . ?
C21 O4 B1 118.15(18) . . ?
C21 O5 B2 120.15(18) . . ?
C2 C1 C6 115.4(2) . . ?
C2 C1 B1 126.3(2) . . ?
C6 C1 B1 118.2(2) . . ?
C1 C2 I1 121.50(16) . . ?
C3 C2 I1 115.38(17) . . ?
C3 C2 C1 123.1(2) . . ?
C4 C3 C2 119.4(2) . . ?
C3 C4 C5 119.8(2) . . ?
C4 C5 C6 119.8(2) . . ?
C5 C6 C1 122.5(2) . . ?
C8 C7 C12 115.6(2) . . ?
C8 C7 B2 124.0(2) . . ?
C12 C7 B2 120.3(2) . . ?
C7 C8 I2 122.22(17) . . ?
C9 C8 I2 115.08(17) . . ?
C9 C8 C7 122.7(2) . . ?
C10 C9 C8 119.5(2) . . ?
C11 C10 C9 119.9(2) . . ?
C10 C11 C12 119.8(2) . . ?
C11 C12 C7 122.4(2) . . ?
O2 C13 O3 123.6(2) . . ?
O2 C13 C14 118.3(2) . . ?
O3 C13 C14 118.0(2) . . ?
C13 C14 C15 108.64(18) . . ?
C16 C15 C14 119.7(2) . . ?
C20 C15 C14 121.1(2) . . ?
C20 C15 C16 119.1(2) . . ?
C17 C16 C15 120.5(2) . . ?
C18 C17 C16 120.1(2) . . ?
C17 C18 C19 120.1(2) . . ?
C18 C19 C20 120.2(3) . . ?
C15 C20 C19 120.0(2) . . ?
O4 C21 O5 123.7(2) . . ?
O4 C21 C22 117.7(2) . . ?
O5 C21 C22 118.6(2) . . ?
C21 C22 C23 113.99(19) . . ?
C24 C23 C22 121.2(2) . . ?
C24 C23 C28 119.4(2) . . ?
C28 C23 C22 119.4(2) . . ?
C23 C24 C25 119.7(3) . . ?
C26 C25 C24 120.1(3) . . ?
C27 C26 C25 120.3(3) . . ?
C26 C27 C28 120.2(3) . . ?
C27 C28 C23 120.3(3) . . ?
O1 B1 O2 109.09(18) . . ?
O1 B1 O4 108.61(18) . . ?
O1 B1 C1 118.13(19) . . ?
O2 B1 C1 107.74(17) . . ?
O4 B1 O2 102.55(16) . . ?
O4 B1 C1 109.59(18) . . ?
O1 B2 O3 109.39(18) . . ?
O1 B2 O5 109.15(18) . . ?
O1 B2 C7 118.47(19) . . ?
O3 B2 O5 101.05(16) . . ?
O3 B2 C7 108.68(18) . . ?
O5 B2 C7 108.69(18) . . ?

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
C1 B1 O2 C13 -145.81(19) . . . . ?
C1 B1 O4 C21 163.42(19) . . . . ?
C2 C1 B1 O1 -177.2(2) . . . . ?
C2 C1 B1 O2 -53.1(3) . . . . ?
C2 C1 B1 O4 57.7(3) . . . . ?
C6 C1 B1 O1 -0.8(3) . . . . ?
C6 C1 B1 O2 123.3(2) . . . . ?
C6 C1 B1 O4 -125.9(2) . . . . ?
C7 B2 O3 C13 163.67(18) . . . . ?
C7 B2 O5 C21 -143.4(2) . . . . ?
C8 C7 B2 O1 -61.7(3) . . . . ?
C8 C7 B2 O3 172.74(19) . . . . ?
C8 C7 B2 O5 63.6(3) . . . . ?
C12 C7 B2 O1 115.9(2) . . . . ?
C12 C7 B2 O3 -9.7(3) . . . . ?
C12 C7 B2 O5 -118.9(2) . . . . ?
C13 O2 B1 O1 -16.4(3) . . . . ?
C13 O2 B1 O4 98.6(2) . . . . ?
C13 O3 B2 O1 32.9(3) . . . . ?
C13 O3 B2 O5 -82.1(2) . . . . ?
C13 C14 C15 C16 -86.1(3) . . . . ?
C13 C14 C15 C20 93.5(3) . . . . ?
C15 C14 C13 O2 90.8(2) . . . . ?
C15 C14 C13 O3 -86.1(2) . . . . ?
C21 O4 B1 O1 33.0(3) . . . . ?
C21 O4 B1 O2 -82.3(2) . . . . ?
C21 O5 B2 O1 -12.9(3) . . . . ?
C21 O5 B2 O3 102.3(2) . . . . ?
C21 C22 C23 C24 58.2(3) . . . . ?
C21 C22 C23 C28 -124.5(2) . . . . ?
C23 C22 C21 O4 -130.9(2) . . . . ?
C23 C22 C21 O5 49.9(3) . . . . ?
B1 O1 B2 O3 -59.2(2) . . . . ?
B1 O1 B2 O5 50.5(2) . . . . ?
B1 O1 B2 C7 175.52(19) . . . . ?
B1 O2 C13 O3 -9.8(3) . . . . ?
B1 O2 C13 C14 173.48(18) . . . . ?
B1 O4 C21 O5 4.4(3) . . . . ?
B1 O4 C21 C22 -174.70(19) . . . . ?
B2 O1 B1 O2 50.8(2) . . . . ?
B2 O1 B1 O4 -60.2(2) . . . . ?
B2 O1 B1 C1 174.23(19) . . . . ?
B2 O3 C13 O2 1.4(3) . . . . ?
B2 O3 C13 C14 178.10(18) . . . . ?
B2 O5 C21 O4 -14.7(3) . . . . ?
B2 O5 C21 C22 164.4(2) . . . . ?

_shelx_SHELXL_version_number     2014/7

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform, pentane'
####################################################################### 
# 
# 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_5d_16srv084
_database_code_depnum_ccdc_archive 'CCDC 1551619'
_audit_update_record             
;
2017-08-09 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2016-03-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;

_chemical_name_common            ?
_chemical_name_systematic        
'Bis-(2-chlorophenyl)borinic acid benzylamine-4-phenylbutanoat '
_chemical_formula_moiety         'C29 H28 B Cl2 N O2'
_chemical_formula_sum            'C29 H28 B Cl2 N O2'
_chemical_formula_weight         504.23
_chemical_melting_point          409.7(5)
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'
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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2006(2)
_cell_length_b                   11.4729(4)
_cell_length_c                   13.1121(4)
_cell_angle_alpha                101.570(3)
_cell_angle_beta                 99.773(2)
_cell_angle_gamma                98.085(3)
_cell_volume                     1314.23(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4447
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.3480
_cell_measurement_theta_min      2.6960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.108
0.00 1.00 0.00 0.108
-1.00 0.00 1.00 0.184
1.00 0.00 -1.00 0.184
-1.00 0.00 -4.00 0.083
1.00 0.00 4.00 0.083

_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.516
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.15
_diffrn_detector_type            'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -41.00   49.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -      -20.1554   57.0000   90.0000 180

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   22.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -      -20.1554 -100.0000 -150.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   63.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804 -100.0000   60.0000 174

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   97.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804  178.0000 -150.0000 124

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   90.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804   57.0000  -30.0000 182

#__ type_ start__ end____ width___ exp.time_
  6 omega   -5.00   93.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804   38.0000 -120.0000 196

#__ type_ start__ end____ width___ exp.time_
  7 omega   -5.00   93.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804   38.0000  150.0000 196

#__ type_ start__ end____ width___ exp.time_
  8 omega  -52.00   46.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804  -38.0000 -150.0000 196
;
_diffrn_measurement_device       kappa-diffractometer
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0738281000
_diffrn_orient_matrix_UB_12      -0.0103236000
_diffrn_orient_matrix_UB_13      0.0095209000
_diffrn_orient_matrix_UB_21      -0.0295983000
_diffrn_orient_matrix_UB_22      -0.0054464000
_diffrn_orient_matrix_UB_23      -0.0546820000
_diffrn_orient_matrix_UB_31      -0.0000004000
_diffrn_orient_matrix_UB_32      -0.0630948000
_diffrn_orient_matrix_UB_33      -0.0100326000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4561
_reflns_number_total             6009
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.029
_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)+(0.0540P)²+0.4430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1263
_refine_special_details          
;
 Amino H atoms - refall, other H atoms - riding (constr).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N(HA,HB), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29)
;
_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 0.31756(6) 0.02519(4) 0.40959(4) 0.03316(14) Uani 1 1 d . . . . .
Cl2 Cl 0.49928(6) 0.24304(5) 0.12179(4) 0.03302(14) Uani 1 1 d . . . . .
O1 O 0.58768(14) 0.23844(11) 0.48657(10) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.50736(16) 0.40256(12) 0.56249(11) 0.0304(3) Uani 1 1 d . . . . .
N N 0.60901(17) 0.38361(14) 0.36830(12) 0.0227(3) Uani 1 1 d . . . . .
HA H 0.5894 0.3884 0.3006 0.027 Uiso 1 1 calc R . . . .
HB H 0.5650 0.4377 0.4045 0.027 Uiso 1 1 calc R . . . .
C1 C 0.5568(2) 0.31081(17) 0.56860(14) 0.0231(4) Uani 1 1 d . . . . .
C2 C 0.5874(2) 0.26814(18) 0.67031(15) 0.0288(4) Uani 1 1 d . . . . .
H2A H 0.6869 0.2479 0.6799 0.035 Uiso 1 1 calc R . . . .
H2B H 0.5160 0.1950 0.6639 0.035 Uiso 1 1 calc R . . . .
C3 C 0.5772(3) 0.3609(2) 0.76821(16) 0.0418(6) Uani 1 1 d . . . . .
H3A H 0.4859 0.3932 0.7532 0.050 Uiso 1 1 calc R . . . .
H3B H 0.6612 0.4274 0.7829 0.050 Uiso 1 1 calc R . . . .
C4 C 0.5775(3) 0.3094(2) 0.86734(17) 0.0409(6) Uani 1 1 d . . . . .
H4A H 0.5655 0.3724 0.9252 0.049 Uiso 1 1 calc R . . . .
H4B H 0.4915 0.2446 0.8531 0.049 Uiso 1 1 calc R . . . .
C5 C 0.7172(3) 0.2612(2) 0.90279(15) 0.0361(5) Uani 1 1 d . . . . .
C6 C 0.8403(3) 0.3388(3) 0.97056(19) 0.0606(8) Uani 1 1 d . . . . .
H6 H 0.8361 0.4202 0.9928 0.073 Uiso 1 1 calc R . . . .
C7 C 0.9668(4) 0.2979(5) 1.0049(3) 0.0906(14) Uani 1 1 d . . . . .
H7 H 1.0480 0.3513 1.0507 0.109 Uiso 1 1 calc R . . . .
C8 C 0.9758(4) 0.1784(6) 0.9727(3) 0.0991(17) Uani 1 1 d . . . . .
H8 H 1.0629 0.1507 0.9963 0.119 Uiso 1 1 calc R . . . .
C9 C 0.8529(4) 0.0976(4) 0.9035(2) 0.0738(11) Uani 1 1 d . . . . .
H9 H 0.8581 0.0163 0.8811 0.089 Uiso 1 1 calc R . . . .
C10 C 0.7242(3) 0.1403(2) 0.86933(18) 0.0435(6) Uani 1 1 d . . . . .
H10 H 0.6422 0.0876 0.8238 0.052 Uiso 1 1 calc R . . . .
C11 C 0.3518(2) 0.23834(17) 0.34527(14) 0.0240(4) Uani 1 1 d . . . . .
C12 C 0.2521(2) 0.13982(18) 0.35517(15) 0.0284(4) Uani 1 1 d . . . . .
C13 C 0.0970(2) 0.1248(2) 0.32284(17) 0.0349(5) Uani 1 1 d . . . . .
H13 H 0.0355 0.0568 0.3304 0.042 Uiso 1 1 calc R . . . .
C14 C 0.0352(2) 0.2109(2) 0.27981(17) 0.0367(5) Uani 1 1 d . . . . .
H14 H -0.0680 0.2009 0.2567 0.044 Uiso 1 1 calc R . . . .
C15 C 0.1283(2) 0.3124(2) 0.27120(16) 0.0346(5) Uani 1 1 d . . . . .
H15 H 0.0871 0.3722 0.2441 0.042 Uiso 1 1 calc R . . . .
C16 C 0.2817(2) 0.32575(19) 0.30251(15) 0.0294(4) Uani 1 1 d . . . . .
H16 H 0.3417 0.3948 0.2954 0.035 Uiso 1 1 calc R . . . .
C17 C 0.5978(2) 0.15191(17) 0.29660(15) 0.0236(4) Uani 1 1 d . . . . .
C18 C 0.5883(2) 0.14209(18) 0.18783(15) 0.0271(4) Uani 1 1 d . . . . .
C19 C 0.6452(2) 0.0563(2) 0.12236(16) 0.0335(5) Uani 1 1 d . . . . .
H19 H 0.6381 0.0555 0.0506 0.040 Uiso 1 1 calc R . . . .
C20 C 0.7125(2) -0.0274(2) 0.16616(18) 0.0358(5) Uani 1 1 d . . . . .
H20 H 0.7510 -0.0857 0.1239 0.043 Uiso 1 1 calc R . . . .
C21 C 0.7224(2) -0.02430(19) 0.27310(18) 0.0335(5) Uani 1 1 d . . . . .
H21 H 0.7657 -0.0817 0.3026 0.040 Uiso 1 1 calc R . . . .
C22 C 0.6678(2) 0.06447(17) 0.33634(16) 0.0272(4) Uani 1 1 d . . . . .
H22 H 0.6781 0.0662 0.4084 0.033 Uiso 1 1 calc R . . . .
C23 C 0.7746(2) 0.41848(17) 0.40888(16) 0.0265(4) Uani 1 1 d . . . . .
H23A H 0.8218 0.3501 0.3859 0.032 Uiso 1 1 calc R . . . .
H23B H 0.7954 0.4388 0.4860 0.032 Uiso 1 1 calc R . . . .
C24 C 0.8409(2) 0.52483(17) 0.36974(16) 0.0256(4) Uani 1 1 d . . . . .
C25 C 0.8896(2) 0.63791(19) 0.43773(17) 0.0333(5) Uani 1 1 d . . . . .
H25 H 0.8794 0.6491 0.5082 0.040 Uiso 1 1 calc R . . . .
C26 C 0.9534(3) 0.7349(2) 0.4016(2) 0.0425(6) Uani 1 1 d . . . . .
H26 H 0.9873 0.8101 0.4484 0.051 Uiso 1 1 calc R . . . .
C27 C 0.9670(3) 0.7205(2) 0.2970(2) 0.0430(6) Uani 1 1 d . . . . .
H27 H 1.0107 0.7853 0.2732 0.052 Uiso 1 1 calc R . . . .
C28 C 0.9148(3) 0.6086(2) 0.2278(2) 0.0441(6) Uani 1 1 d . . . . .
H28 H 0.9213 0.5987 0.1566 0.053 Uiso 1 1 calc R . . . .
C29 C 0.8528(3) 0.5112(2) 0.26404(17) 0.0347(5) Uani 1 1 d . . . . .
H29 H 0.8189 0.4361 0.2171 0.042 Uiso 1 1 calc R . . . .
B B 0.5331(2) 0.25074(19) 0.37547(16) 0.0223(4) 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
Cl1 C12 1.748(2) . ?
Cl2 C18 1.786(2) . ?
O1 C1 1.319(2) . ?
O1 B 1.499(2) . ?
O2 C1 1.216(2) . ?
N C23 1.494(2) . ?
N B 1.613(3) . ?
C1 C2 1.507(3) . ?
C2 C3 1.520(3) . ?
C3 C4 1.532(3) . ?
C4 C5 1.509(3) . ?
C5 C6 1.387(3) . ?
C5 C10 1.382(3) . ?
C6 C7 1.355(5) . ?
C7 C8 1.370(6) . ?
C8 C9 1.407(6) . ?
C9 C10 1.384(4) . ?
C11 C12 1.394(3) . ?
C11 C16 1.422(3) . ?
C11 B 1.626(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.374(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.379(3) . ?
C17 C18 1.395(3) . ?
C17 C22 1.404(3) . ?
C17 B 1.624(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.379(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.387(3) . ?
C23 C24 1.508(3) . ?
C24 C25 1.384(3) . ?
C24 C29 1.388(3) . ?
C25 C26 1.389(3) . ?
C26 C27 1.377(3) . ?
C27 C28 1.383(3) . ?
C28 C29 1.388(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
C1 O1 B 120.69(15) . . ?
C23 N B 116.22(14) . . ?
O1 C1 C2 113.50(16) . . ?
O2 C1 O1 123.20(17) . . ?
O2 C1 C2 123.30(17) . . ?
C1 C2 C3 113.60(17) . . ?
C2 C3 C4 113.43(18) . . ?
C5 C4 C3 114.5(2) . . ?
C6 C5 C4 119.7(2) . . ?
C10 C5 C4 121.0(2) . . ?
C10 C5 C6 119.3(3) . . ?
C7 C6 C5 121.1(3) . . ?
C6 C7 C8 120.4(3) . . ?
C7 C8 C9 119.8(3) . . ?
C10 C9 C8 119.3(3) . . ?
C5 C10 C9 120.1(3) . . ?
C12 C11 C16 114.22(18) . . ?
C12 C11 B 123.31(17) . . ?
C16 C11 B 122.43(18) . . ?
C11 C12 Cl1 120.75(15) . . ?
C13 C12 Cl1 115.71(17) . . ?
C13 C12 C11 123.5(2) . . ?
C14 C13 C12 119.8(2) . . ?
C13 C14 C15 119.2(2) . . ?
C16 C15 C14 120.5(2) . . ?
C15 C16 C11 122.7(2) . . ?
C18 C17 C22 114.11(17) . . ?
C18 C17 B 125.87(17) . . ?
C22 C17 B 120.00(16) . . ?
C17 C18 Cl2 120.85(15) . . ?
C19 C18 Cl2 114.67(15) . . ?
C19 C18 C17 124.48(19) . . ?
C20 C19 C18 118.6(2) . . ?
C19 C20 C21 119.78(19) . . ?
C20 C21 C22 119.9(2) . . ?
C21 C22 C17 123.07(19) . . ?
N C23 C24 111.83(15) . . ?
C25 C24 C23 120.94(18) . . ?
C25 C24 C29 118.68(19) . . ?
C29 C24 C23 120.38(17) . . ?
C24 C25 C26 120.6(2) . . ?
C27 C26 C25 120.5(2) . . ?
C26 C27 C28 119.4(2) . . ?
C27 C28 C29 120.2(2) . . ?
C24 C29 C28 120.6(2) . . ?
O1 B N 107.01(14) . . ?
O1 B C11 112.72(16) . . ?
O1 B C17 107.00(15) . . ?
N B C11 108.56(15) . . ?
N B C17 107.88(16) . . ?
C17 B C11 113.39(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N HA Cl2 0.89 2.52 3.2265(16) 136.9 .
N HB O2 0.89 2.03 2.857(2) 154.6 2_666

_shelx_SHELXL_version_number     2014/7
####################################################################### 
# 
# 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_5b_15srv006
_database_code_depnum_ccdc_archive 'CCDC 1551617'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2017-07-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number     2016/6

_chemical_name_common            ?
_chemical_name_systematic        
'Bis(3,4,5-trifluorophenyl)-borinic acid benzylaminobenzoat'
_chemical_formula_moiety         'C26 H18 B F6 N O2'
_chemical_formula_sum            'C26 H18 B F6 N O2'
_chemical_formula_weight         501.22
_chemical_melting_point          471.7(1.5)
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.1019(4)
_cell_length_b                   11.7656(5)
_cell_length_c                   19.5670(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.6902(15)
_cell_angle_gamma                90
_cell_volume                     2259.56(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0617 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.9356.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedron
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 1.00 0.0030
0.00 1.00 -1.00 0.1190
-1.00 -3.00 3.00 0.0230
1.00 3.00 -3.00 0.1600
0.00 1.00 1.00 0.1460
-1.00 -3.00 1.00 0.0220
0.00 -1.00 -3.00 0.0800
-1.00 1.00 -3.00 0.0980
1.00 2.00 2.00 0.1540
1.00 -2.00 2.00 0.0230
-2.00 3.00 1.00 0.1370
2.00 -2.00 -1.00 0.0460
-3.00 0.00 1.00 0.1120
3.00 0.00 -1.00 0.1320
1.00 -1.00 -2.00 0.0490

_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.243
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29313
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4345
_reflns_number_total             5189
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5189
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.012
_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)+(0.0440P)²+1.0370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0976
_refine_special_details          
;
 Phenyl substituent at C(1) shows flipping disorder, which was 
rationalised as two alternative positions for C(4), C(5), C(6),  
C(7) and their hydrogens, with occupancies refined to 0.655(8) 
and 0.345(8). 
Amino H atoms: refall, other H atoms: riding model (constr).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C4A-C3 \\sim C4-C3
 with sigma of 0.02
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 C7-C2 \\sim C7A-C2
 with sigma of 0.02
 C7-C6 \\sim C7A-C6A
 with sigma of 0.02
 C6-C5 \\sim C6A-C5A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
Uanis(C7) = Uanis(C7A)
4. Rigid body (RIGU) restrains
 C2, C3, C4, C5, C6, C7, C4A, C5A, C6A, C7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=1-
 FVAR(1)
 Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=FVAR(1)
 Fixed Sof: H3B(0.6) H3A(0.4)
6.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3B), C3(H3A), C9(H9), C13(H13), C15(H15), C19(H19), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C4(H4), C5(H5), C6(H6), C7(H7), C4A(H4A),
 C5A(H5A), C6A(H6A), C7A(H7A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.61098(11) 0.52102(8) 0.12885(5) 0.0446(2) Uani 1 1 d . . . . .
F2 F 0.77321(9) 0.34069(8) 0.12051(4) 0.0366(2) Uani 1 1 d . . . . .
F3 F 0.81047(8) 0.17785(7) 0.21906(4) 0.0333(2) Uani 1 1 d . . . . .
F4 F 0.13296(8) 0.65335(8) 0.30983(5) 0.0388(2) Uani 1 1 d . . . . .
F5 F -0.03428(8) 0.47521(9) 0.26732(5) 0.0444(2) Uani 1 1 d . . . . .
F6 F 0.07096(10) 0.26332(9) 0.26884(5) 0.0495(3) Uani 1 1 d . . . . .
O1 O 0.57651(9) 0.29427(7) 0.40671(4) 0.02166(19) Uani 1 1 d . . . . .
O2 O 0.50199(10) 0.36816(8) 0.49618(5) 0.0297(2) Uani 1 1 d . . . . .
N1 N 0.62540(10) 0.50364(9) 0.40316(6) 0.0197(2) Uani 1 1 d . . . . .
H1A H 0.6238(15) 0.5628(14) 0.3731(8) 0.026(4) Uiso 1 1 d . . . . .
H1B H 0.5813(17) 0.5320(14) 0.4361(9) 0.032(4) Uiso 1 1 d . . . . .
C1 C 0.55280(13) 0.29004(11) 0.47039(6) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.59971(13) 0.18264(11) 0.50843(6) 0.0227(3) Uani 1 1 d D U . . .
C3 C 0.66770(15) 0.09986(13) 0.48016(7) 0.0319(3) Uani 1 1 d D U . . .
H3B H 0.669117 0.104817 0.431880 0.038 Uiso 0.6 1 calc R . P A 2
H3A H 0.686686 0.110970 0.435344 0.038 Uiso 0.4 1 calc R . P B 1
C8 C 0.60188(12) 0.37505(10) 0.29205(6) 0.0197(2) Uani 1 1 d . . . . .
C9 C 0.57515(14) 0.45415(11) 0.23719(7) 0.0241(3) Uani 1 1 d . . . . .
H9 H 0.516480 0.516615 0.238972 0.029 Uiso 1 1 calc R . . . .
C10 C 0.63313(14) 0.44232(12) 0.18058(7) 0.0273(3) Uani 1 1 d . . . . .
C11 C 0.71445(13) 0.35090(12) 0.17512(7) 0.0254(3) Uani 1 1 d . . . . .
C12 C 0.73502(12) 0.26996(11) 0.22693(7) 0.0230(3) Uani 1 1 d . . . . .
C13 C 0.68254(12) 0.28116(11) 0.28549(6) 0.0217(3) Uani 1 1 d . . . . .
H13 H 0.701216 0.225021 0.321382 0.026 Uiso 1 1 calc R . . . .
C14 C 0.38210(13) 0.42380(11) 0.33925(6) 0.0213(3) Uani 1 1 d . . . . .
C15 C 0.32558(13) 0.53206(12) 0.33729(7) 0.0239(3) Uani 1 1 d . . . . .
H15 H 0.382890 0.595546 0.352879 0.029 Uiso 1 1 calc R . . . .
C16 C 0.18678(14) 0.54798(12) 0.31287(7) 0.0273(3) Uani 1 1 d . . . . .
C17 C 0.10057(13) 0.45802(14) 0.29085(7) 0.0301(3) Uani 1 1 d . . . . .
C18 C 0.15585(14) 0.35121(14) 0.29222(7) 0.0316(3) Uani 1 1 d . . . . .
C19 C 0.29368(14) 0.33291(12) 0.31551(7) 0.0270(3) Uani 1 1 d . . . . .
H19 H 0.329107 0.258123 0.315490 0.032 Uiso 1 1 calc R . . . .
C20 C 0.77200(13) 0.47863(11) 0.43760(7) 0.0260(3) Uani 1 1 d . . . . .
H20A H 0.775860 0.427444 0.478179 0.031 Uiso 1 1 calc R . . . .
H20B H 0.814030 0.438379 0.403626 0.031 Uiso 1 1 calc R . . . .
C21 C 0.85307(12) 0.58405(11) 0.46259(6) 0.0218(3) Uani 1 1 d . . . . .
C22 C 0.94046(13) 0.62906(12) 0.42440(7) 0.0244(3) Uani 1 1 d . . . . .
H22 H 0.948087 0.593233 0.381993 0.029 Uiso 1 1 calc R . . . .
C23 C 1.01669(13) 0.72563(12) 0.44745(7) 0.0280(3) Uani 1 1 d . . . . .
H23 H 1.076387 0.755493 0.421005 0.034 Uiso 1 1 calc R . . . .
C24 C 1.00559(14) 0.77844(12) 0.50909(7) 0.0296(3) Uani 1 1 d . . . . .
H24 H 1.056954 0.845047 0.524838 0.036 Uiso 1 1 calc R . . . .
C25 C 0.91934(15) 0.73378(12) 0.54769(7) 0.0304(3) Uani 1 1 d . . . . .
H25 H 0.912169 0.769641 0.590164 0.037 Uiso 1 1 calc R . . . .
C26 C 0.84351(14) 0.63727(12) 0.52479(7) 0.0264(3) Uani 1 1 d . . . . .
H26 H 0.784653 0.607180 0.551635 0.032 Uiso 1 1 calc R . . . .
B1 B 0.54306(14) 0.39655(12) 0.36095(7) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.7084(8) 0.0000(8) 0.5175(5) 0.0336(13) Uani 0.655(8) 1 d D U P C 1
H4 H 0.751866 -0.059000 0.497823 0.040 Uiso 0.655(8) 1 calc R . P C 1
C5 C 0.6844(6) -0.0114(7) 0.5834(4) 0.0382(12) Uani 0.655(8) 1 d D U P C 1
H5 H 0.721813 -0.074505 0.611757 0.046 Uiso 0.655(8) 1 calc R . P C 1
C6 C 0.6065(6) 0.0676(3) 0.60933(18) 0.0412(9) Uani 0.655(8) 1 d D U P C 1
H6 H 0.584042 0.054495 0.653158 0.049 Uiso 0.655(8) 1 calc R . P C 1
C7 C 0.5614(5) 0.1654(3) 0.5716(2) 0.0295(8) Uani 0.655(8) 1 d D U P C 1
H7 H 0.506016 0.219069 0.588151 0.035 Uiso 0.655(8) 1 calc R . P C 1
C4A C 0.7339(19) 0.0099(15) 0.5195(10) 0.0336(13) Uani 0.345(8) 1 d D U P C 2
H4A H 0.788790 -0.039227 0.499286 0.040 Uiso 0.345(8) 1 calc R . P C 2
C5A C 0.7225(13) -0.0101(14) 0.5865(8) 0.0382(12) Uani 0.345(8) 1 d D U P C 2
H5A H 0.751679 -0.079848 0.609626 0.046 Uiso 0.345(8) 1 calc R . P C 2
C6A C 0.6680(9) 0.0733(7) 0.6185(4) 0.0412(9) Uani 0.345(8) 1 d D U P C 2
H6A H 0.669228 0.066889 0.667055 0.049 Uiso 0.345(8) 1 calc R . P C 2
C7A C 0.6105(8) 0.1677(8) 0.5812(4) 0.0295(8) Uani 0.345(8) 1 d D U P C 2
H7A H 0.576230 0.226043 0.605886 0.035 Uiso 0.345(8) 1 calc R . P C 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
F1 C10 1.3508(15) . ?
F2 C11 1.3450(14) . ?
F3 C12 1.3546(15) . ?
F4 C16 1.3493(16) . ?
F5 C17 1.3460(15) . ?
F6 C18 1.3521(16) . ?
O1 C1 1.3243(14) . ?
O1 B1 1.4902(16) . ?
O2 C1 1.2189(16) . ?
N1 C20 1.5039(16) . ?
N1 B1 1.6238(17) . ?
C1 C2 1.4861(18) . ?
C2 C3 1.3806(19) . ?
C2 C7 1.394(4) . ?
C2 C7A 1.414(8) . ?
C3 C4 1.394(7) . ?
C3 C4A 1.384(13) . ?
C8 C9 1.3979(17) . ?
C8 C13 1.3966(17) . ?
C8 B1 1.6167(18) . ?
C9 C10 1.3771(18) . ?
C10 C11 1.373(2) . ?
C11 C12 1.3704(19) . ?
C12 C13 1.3779(17) . ?
C14 C15 1.3928(19) . ?
C14 C19 1.4002(18) . ?
C14 B1 1.6125(18) . ?
C15 C16 1.3828(18) . ?
C16 C17 1.374(2) . ?
C17 C18 1.373(2) . ?
C18 C19 1.376(2) . ?
C20 C21 1.5029(18) . ?
C21 C22 1.3894(18) . ?
C21 C26 1.3921(18) . ?
C22 C23 1.3868(19) . ?
C23 C24 1.385(2) . ?
C24 C25 1.385(2) . ?
C25 C26 1.384(2) . ?
C4 C5 1.373(7) . ?
C5 C6 1.390(6) . ?
C6 C7 1.385(5) . ?
C4A C5A 1.362(13) . ?
C5A C6A 1.350(12) . ?
C6A C7A 1.380(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 B1 122.00(10) . . ?
C20 N1 B1 114.06(10) . . ?
O1 C1 C2 113.33(11) . . ?
O2 C1 O1 123.29(12) . . ?
O2 C1 C2 123.33(11) . . ?
C3 C2 C1 121.94(11) . . ?
C3 C2 C7 121.4(2) . . ?
C3 C2 C7A 112.9(4) . . ?
C7 C2 C1 116.4(2) . . ?
C7A C2 C1 123.3(4) . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 C4A 122.5(9) . . ?
C9 C8 B1 119.60(11) . . ?
C13 C8 C9 117.83(11) . . ?
C13 C8 B1 122.55(11) . . ?
C10 C9 C8 120.59(12) . . ?
F1 C10 C9 120.45(13) . . ?
F1 C10 C11 118.35(12) . . ?
C11 C10 C9 121.19(12) . . ?
F2 C11 C10 121.10(12) . . ?
F2 C11 C12 120.50(12) . . ?
C12 C11 C10 118.41(11) . . ?
F3 C12 C11 117.57(11) . . ?
F3 C12 C13 120.57(12) . . ?
C11 C12 C13 121.86(12) . . ?
C12 C13 C8 119.99(12) . . ?
C15 C14 C19 117.65(12) . . ?
C15 C14 B1 124.78(11) . . ?
C19 C14 B1 117.38(12) . . ?
C16 C15 C14 120.59(13) . . ?
F4 C16 C15 120.31(13) . . ?
F4 C16 C17 118.37(12) . . ?
C17 C16 C15 121.32(13) . . ?
F5 C17 C16 120.45(14) . . ?
F5 C17 C18 121.21(13) . . ?
C18 C17 C16 118.32(12) . . ?
F6 C18 C17 118.10(13) . . ?
F6 C18 C19 120.24(14) . . ?
C17 C18 C19 121.66(13) . . ?
C18 C19 C14 120.44(13) . . ?
C21 C20 N1 112.79(10) . . ?
C22 C21 C20 120.41(12) . . ?
C22 C21 C26 118.89(12) . . ?
C26 C21 C20 120.69(12) . . ?
C23 C22 C21 120.80(12) . . ?
C24 C23 C22 119.85(13) . . ?
C25 C24 C23 119.73(13) . . ?
C26 C25 C24 120.43(13) . . ?
C25 C26 C21 120.30(13) . . ?
O1 B1 N1 107.76(9) . . ?
O1 B1 C8 107.39(10) . . ?
O1 B1 C14 112.94(10) . . ?
C8 B1 N1 107.49(10) . . ?
C14 B1 N1 110.05(10) . . ?
C14 B1 C8 110.99(10) . . ?
C5 C4 C3 118.6(9) . . ?
C4 C5 C6 121.2(8) . . ?
C7 C6 C5 120.3(5) . . ?
C6 C7 C2 117.9(3) . . ?
C5A C4A C3 121.8(17) . . ?
C6A C5A C4A 117.2(17) . . ?
C5A C6A C7A 120.4(10) . . ?
C6A C7A C2 123.7(7) . . ?

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
N1 H1B O2 0.928(17) 2.091(18) 3.0016(14) 166.8(15) 3_666
C23 H23 F4 0.95 2.66 3.2941(17) 124.4 1_655

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# 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_4b_15srv104
_database_code_depnum_ccdc_archive 'CCDC 1551615'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2015-04-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;

_chemical_name_common            ?
_chemical_name_systematic        
; Bis-3,4,5-trifluorophenylborinic acid ethylenediamine complex 
;
_chemical_formula_moiety         'C14 H13 B F6 N2 O,0.5(C D Cl3)'
_chemical_formula_sum            'C14.5 H13 B Cl1.5 D0.5 F6 N2 O'
_chemical_formula_weight         410.26
_chemical_absolute_configuration ?
_chemical_melting_point          363.7(2.5)
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'
D D 0.0000 0.0000 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.7500(5)
_cell_length_b                   11.0269(4)
_cell_length_c                   13.1973(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.3307(14)
_cell_angle_gamma                90
_cell_volume                     1695.95(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.27
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1159 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.9440.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             828
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 2.00 -1.00 0.1490
-1.00 0.00 2.00 0.1030
1.00 1.00 -2.00 0.1510
-1.00 1.00 1.00 0.1680
0.00 2.00 -1.00 0.2330
3.00 0.00 -2.00 0.1620
-1.00 -1.00 2.00 0.1290
-2.00 -1.00 3.00 0.1060
-1.00 2.00 -1.00 0.2440
-1.00 0.00 1.00 0.1110
-3.00 2.00 1.00 0.1900
3.00 -1.00 -2.00 0.1730
0.00 -1.00 1.00 0.1680
1.00 -2.00 -3.00 0.1020
0.00 -3.00 -1.00 0.1310
0.00 3.00 1.00 0.1930
-3.00 1.00 -2.00 0.2180
0.00 1.00 -2.00 0.1800
3.00 1.00 -1.00 0.1800
0.00 -1.00 3.00 0.1850
-3.00 -1.00 1.00 0.1800
0.00 1.00 -3.00 0.1700
-1.00 0.00 -3.00 0.1520
3.00 1.00 3.00 0.2200
1.00 2.00 3.00 0.1370
0.00 -2.00 -3.00 0.0840

_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.274
_exptl_special_details           
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of narrow-frame ω-scans (scan 
width 0.5°, 10s exposure), every run at a different φ angle.
One run of φ-scans (scan width 1°, 1s exposure) was used for 
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_exptl_twin_twinlaw_details      '-1 0 0 0 -1 0 0 0 -1'
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35272
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.325
_diffrn_reflns_theta_min         2.415
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                8294
_reflns_number_total             9254
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.39(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         9254
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.042
_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)+(0.0770P)²+0.7700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1267
_refine_special_details          
;Refined as a 2-component inversion twin, BASF = 0.39(10). 
The CDCl₃ molecule is disordered. The minor orientation (15%) 
comprises C(2S), D(2), Cl(6), Cl(7) and Cl(8). The major 
orientation includes C(1S) with D(1) and Cl(1) (85%), while 
two other Cl atoms are further disordered: Cl(2) and Cl(3) have 
occupancies of 70%, Cl(4) and Cl(5) of 15%. 
One trifluorophenyl group at B(1) shows a flipping disorder: 
C(4), C(5), C(6), F(2) and F(3) are disordered between positions 
A and B with occupancies refined to 57.8(8) and 42.2(8)%, 
respectively. Hydroxyl and amino H atoms - refall, other H atoms 
- riding model (constr).,Twin
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.61(10) 0.39(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
3. Restrained distances
 C6A-C1 \\sim C6B-C1
 with sigma of 0.02
 C4A-C3 \\sim C4B-C3
 with sigma of 0.02
 F2A-C4A \\sim F2B-C4B
 with sigma of 0.02
 Cl4-C1S \\sim Cl2-C1S \\sim Cl3-C1S \\sim Cl5-C1S \\sim Cl1-C1S \\sim Cl8-C2S
\\sim Cl6-C2S \\sim Cl7-C2S
 with sigma of 0.02
 C6A-C5A \\sim C6B-C5B
 with sigma of 0.02
 C5A-C4A \\sim C5B-C4B
 with sigma of 0.02
 F3A-C5A \\sim F3B-C5B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(C6A) = Uiso(C6B)
Uiso(C4B) = Uiso(C4A)
Uanis(F2A) = Uanis(F2B)
Uanis(F3A) = Uanis(F3B)
Uanis(C2S) = Uanis(C1S)
Uanis(C5B) = Uanis(C5A)
5. Rigid body (RIGU) restrains
 F1, C1, C2, C3, F2A, F3A, C4A, C5A, C6A, F2B, F3B, C4B, C5B, C6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F2B)=Sof(F3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=1-FVAR(1)
 Sof(F2A)=Sof(F3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=FVAR(1)
 Fixed Sof: Cl6(0.15) Cl7(0.15) Cl8(0.15) C2S(0.15) D2(0.15) C1S(0.85)
 D1(0.85) Cl1(0.85) Cl2(0.7) Cl3(0.7) Cl4(0.15) Cl5(0.15)
7.a Riding coordinates:
 C2S(D2), C1S(D1), C6A(H6A), C6B(H6B)
7.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C7(H7A,H7B), C8(H8A,H8B)
7.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C22(H22), C26(H26), C2(H2), C10(H10), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl6 Cl -0.0838(10) 0.3964(11) 0.2501(10) 0.047(2) Uiso 0.15 1 d D . P A 3
Cl7 Cl -0.1780(9) 0.1702(8) 0.2722(19) 0.125(8) Uani 0.15 1 d D . P A 3
Cl8 Cl 0.0435(11) 0.2473(9) 0.4143(7) 0.072(3) Uani 0.15 1 d D . P A 3
C2S C -0.0476(19) 0.2452(19) 0.2934(19) 0.0496(13) Uani 0.15 1 d D . P A 3
D2 D -0.0006 0.2119 0.2419 0.060 Uiso 0.15 1 d R . P A 3
C1S C -0.0483(5) 0.2880(5) 0.3630(5) 0.0496(13) Uani 0.85 1 d D . P . .
D1 D -0.0159 0.3330 0.4260 0.060 Uiso 0.85 1 d R . P B 1
Cl1 Cl -0.0429(3) 0.3716(3) 0.2527(2) 0.1037(12) Uani 0.85 1 d D . P C 1
Cl2 Cl -0.1936(2) 0.2955(3) 0.3911(3) 0.0831(8) Uani 0.7 1 d D . P C 1
Cl3 Cl -0.0052(2) 0.14034(18) 0.36495(18) 0.0681(6) Uani 0.7 1 d D . P C 1
Cl4 Cl -0.1688(6) 0.2074(8) 0.3790(7) 0.0441(17) Uani 0.15 1 d D . P C 2
Cl5 Cl 0.0525(9) 0.1727(9) 0.3203(8) 0.057(2) Uiso 0.15 1 d D . P C 2
F7 F 0.5340(2) 1.16908(17) 0.17500(15) 0.0316(5) Uani 1 1 d . . . . .
F8 F 0.5406(2) 1.29059(16) 0.35434(16) 0.0291(5) Uani 1 1 d . . . . .
F9 F 0.58267(19) 1.16952(18) 0.53195(14) 0.0252(4) Uani 1 1 d . . . . .
F10 F 1.03479(18) 0.8811(3) 0.40980(19) 0.0415(6) Uani 1 1 d . . . . .
F11 F 1.0960(2) 0.6671(3) 0.4957(2) 0.0522(8) Uani 1 1 d . . . . .
F12 F 0.9341(2) 0.5006(3) 0.5237(2) 0.0475(7) Uani 1 1 d . . . . .
O2 O 0.53378(18) 0.71442(19) 0.41693(16) 0.0140(4) Uani 1 1 d . . . . .
H2C H 0.559(4) 0.675(4) 0.461(3) 0.017 Uiso 1 1 d R . . . .
N3 N 0.5932(2) 0.7190(2) 0.24470(18) 0.0106(4) Uani 1 1 d . . . . .
H3A H 0.526(3) 0.743(3) 0.215(2) 0.002(7) Uiso 1 1 d . . . . .
H3B H 0.655(4) 0.764(4) 0.202(4) 0.035(12) Uiso 1 1 d . . . . .
N4 N 0.5924(3) 0.4148(2) 0.1078(2) 0.0196(5) Uani 1 1 d . . . . .
H4A H 0.662(4) 0.394(4) 0.138(4) 0.027(11) Uiso 1 1 d . . . . .
H4B H 0.545(5) 0.379(5) 0.135(5) 0.051(16) Uiso 1 1 d . . . . .
C15 C 0.5969(2) 0.9178(2) 0.3535(2) 0.0114(5) Uani 1 1 d . . . . .
C16 C 0.5747(3) 0.9830(3) 0.2620(2) 0.0159(5) Uani 1 1 d . . . . .
H16 H 0.5723 0.9420 0.1984 0.019 Uiso 1 1 calc R . . . .
C17 C 0.5562(3) 1.1067(3) 0.2639(2) 0.0187(6) Uani 1 1 d . . . . .
C18 C 0.5587(3) 1.1697(3) 0.3536(2) 0.0185(6) Uani 1 1 d . . . . .
C19 C 0.5814(3) 1.1061(3) 0.4438(2) 0.0161(6) Uani 1 1 d . . . . .
C20 C 0.6003(2) 0.9826(3) 0.4450(2) 0.0135(5) Uani 1 1 d . . . . .
H20 H 0.6159 0.9412 0.5084 0.016 Uiso 1 1 calc R . . . .
C21 C 0.7516(2) 0.7423(3) 0.4037(2) 0.0135(5) Uani 1 1 d . . . . .
C22 C 0.8379(3) 0.8271(3) 0.3914(2) 0.0189(6) Uani 1 1 d . . . . .
H22 H 0.8180 0.9038 0.3616 0.023 Uiso 1 1 calc R . . . .
C23 C 0.9520(3) 0.7993(4) 0.4227(3) 0.0269(7) Uani 1 1 d . . . . .
C24 C 0.9842(3) 0.6912(4) 0.4665(3) 0.0335(9) Uani 1 1 d . . . . .
C25 C 0.9010(3) 0.6081(4) 0.4799(3) 0.0303(8) Uani 1 1 d . . . . .
C26 C 0.7857(3) 0.6312(3) 0.4489(2) 0.0201(6) Uani 1 1 d . . . . .
H26 H 0.7298 0.5714 0.4584 0.024 Uiso 1 1 calc R . . . .
C27 C 0.6018(3) 0.5851(2) 0.2334(2) 0.0141(5) Uani 1 1 d . . . . .
H27A H 0.5421 0.5455 0.2685 0.017 Uiso 1 1 calc R . . . .
H27B H 0.6777 0.5575 0.2668 0.017 Uiso 1 1 calc R . . . .
C28 C 0.5870(3) 0.5466(3) 0.1211(2) 0.0150(5) Uani 1 1 d . . . . .
H28A H 0.5121 0.5765 0.0875 0.018 Uiso 1 1 calc R . . . .
H28B H 0.6479 0.5851 0.0867 0.018 Uiso 1 1 calc R . . . .
B2 B 0.6181(3) 0.7717(3) 0.3612(2) 0.0104(5) Uani 1 1 d . . . . .
F1 F 0.31953(18) 0.33589(18) 0.07665(15) 0.0251(4) Uani 1 1 d . U . . .
F4 F -0.15455(18) 0.6673(3) 0.1763(2) 0.0440(7) Uani 1 1 d . . . . .
F5 F -0.1925(2) 0.8987(3) 0.1178(2) 0.0524(8) Uani 1 1 d . . . . .
F6 F -0.0124(2) 1.0521(2) 0.11094(19) 0.0447(7) Uani 1 1 d . . . . .
O1 O 0.35998(17) 0.78212(18) 0.19034(16) 0.0131(4) Uani 1 1 d . . . . .
H1 H 0.336(4) 0.830(4) 0.134(4) 0.032(11) Uiso 1 1 d . . . . .
N1 N 0.2996(2) 0.7820(2) 0.36277(18) 0.0109(4) Uani 1 1 d . . . . .
H1A H 0.370(4) 0.756(4) 0.383(4) 0.027(11) Uiso 1 1 d . . . . .
H1B H 0.253(3) 0.752(3) 0.398(3) 0.008(8) Uiso 1 1 d . . . . .
N2 N 0.3080(2) 1.0815(2) 0.5058(2) 0.0185(5) Uani 1 1 d . . . . .
H2A H 0.363(3) 1.123(4) 0.475(3) 0.016(9) Uiso 1 1 d . . . . .
H2B H 0.226(4) 1.114(4) 0.478(4) 0.033(12) Uiso 1 1 d . . . . .
C1 C 0.2792(2) 0.5853(2) 0.2511(2) 0.0128(5) Uani 1 1 d D U . . .
C2 C 0.2945(2) 0.5210(3) 0.1619(2) 0.0151(5) Uani 1 1 d . U . . .
H2 H 0.3006 0.5642 0.1005 0.018 Uiso 1 1 calc R . . . .
C3 C 0.3008(3) 0.3968(3) 0.1621(2) 0.0161(5) Uani 1 1 d D U . . .
C7 C 0.2956(2) 0.9151(2) 0.3781(2) 0.0116(5) Uani 1 1 d . . . . .
H7A H 0.2199 0.9460 0.3472 0.014 Uiso 1 1 calc R . . . .
H7B H 0.3551 0.9541 0.3423 0.014 Uiso 1 1 calc R . . . .
C8 C 0.3148(3) 0.9501(2) 0.4904(2) 0.0142(5) Uani 1 1 d . . . . .
H8A H 0.2565 0.9094 0.5264 0.017 Uiso 1 1 calc R . . . .
H8B H 0.3913 0.9209 0.5208 0.017 Uiso 1 1 calc R . . . .
C9 C 0.1412(2) 0.7765(3) 0.2021(2) 0.0139(5) Uani 1 1 d . . . . .
C10 C 0.0468(3) 0.6997(3) 0.2025(2) 0.0201(6) Uani 1 1 d . . . . .
H10 H 0.0583 0.6177 0.2232 0.024 Uiso 1 1 calc R . . . .
C11 C -0.0633(3) 0.7419(4) 0.1731(3) 0.0287(8) Uani 1 1 d . . . . .
C12 C -0.0842(3) 0.8592(4) 0.1434(3) 0.0327(9) Uani 1 1 d . . . . .
C13 C 0.0080(3) 0.9355(4) 0.1401(3) 0.0286(8) Uani 1 1 d . . . . .
C14 C 0.1191(3) 0.8964(3) 0.1680(2) 0.0185(6) Uani 1 1 d . . . . .
H14 H 0.1813 0.9506 0.1642 0.022 Uiso 1 1 calc R . . . .
B1 B 0.2710(3) 0.7326(3) 0.2447(2) 0.0114(5) Uani 1 1 d . . . . .
F2A F 0.2868(19) 0.2065(11) 0.249(3) 0.031(3) Uani 0.578(8) 1 d D U P D 1
F3A F 0.2424(7) 0.3258(5) 0.4175(4) 0.0411(14) Uani 0.578(8) 1 d D U P D 1
C4A C 0.2808(5) 0.3288(6) 0.2467(5) 0.0166(8) Uiso 0.578(8) 1 d D U P D 1
C5A C 0.2613(9) 0.3912(9) 0.3339(8) 0.023(2) Uani 0.578(8) 1 d D U P D 1
C6A C 0.2567(5) 0.5163(5) 0.3358(4) 0.0135(8) Uiso 0.578(8) 1 d D U P D 1
H6A H 0.2370 0.5563 0.3949 0.016 Uiso 0.578(8) 1 d R . P D 1
F2B F 0.312(3) 0.2100(16) 0.246(4) 0.031(3) Uani 0.422(8) 1 d D U P D 2
F3B F 0.3051(10) 0.3288(7) 0.4264(6) 0.0411(14) Uani 0.422(8) 1 d D U P D 2
C4B C 0.3063(8) 0.3318(8) 0.2494(7) 0.0166(8) Uiso 0.422(8) 1 d D U P D 2
C5B C 0.2975(14) 0.3943(12) 0.3380(11) 0.023(2) Uani 0.422(8) 1 d D U P D 2
C6B C 0.2917(8) 0.5178(7) 0.3424(6) 0.0135(8) Uiso 0.422(8) 1 d D U P D 2
H6B H 0.2916 0.5580 0.4061 0.016 Uiso 0.422(8) 1 d R . P D 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
Cl6 C2S 1.796(19) . ?
Cl7 C2S 1.732(18) . ?
Cl8 C2S 1.805(18) . ?
C1S Cl1 1.731(6) . ?
C1S Cl2 1.795(6) . ?
C1S Cl3 1.704(6) . ?
C1S Cl4 1.708(8) . ?
C1S Cl5 1.873(10) . ?
F7 C17 1.356(3) . ?
F8 C18 1.351(3) . ?
F9 C19 1.356(3) . ?
F10 C23 1.354(4) . ?
F11 C24 1.347(4) . ?
F12 C25 1.354(4) . ?
O2 B2 1.451(4) . ?
N3 C27 1.489(3) . ?
N3 B2 1.635(4) . ?
N4 C28 1.466(4) . ?
C15 C16 1.402(4) . ?
C15 C20 1.398(4) . ?
C15 B2 1.631(4) . ?
C16 C17 1.382(4) . ?
C17 C18 1.370(4) . ?
C18 C19 1.378(4) . ?
C19 C20 1.379(4) . ?
C21 C22 1.404(4) . ?
C21 C26 1.398(4) . ?
C21 B2 1.630(4) . ?
C22 C23 1.386(5) . ?
C23 C24 1.357(6) . ?
C24 C25 1.369(6) . ?
C25 C26 1.388(4) . ?
C27 C28 1.531(4) . ?
F1 C3 1.355(3) . ?
F4 C11 1.356(4) . ?
F5 C12 1.347(4) . ?
F6 C13 1.354(4) . ?
O1 B1 1.447(4) . ?
N1 C7 1.483(3) . ?
N1 B1 1.645(4) . ?
N2 C8 1.467(4) . ?
C1 C2 1.406(4) . ?
C1 B1 1.629(4) . ?
C1 C6A 1.404(6) . ?
C1 C6B 1.408(8) . ?
C2 C3 1.371(4) . ?
C3 C4A 1.389(7) . ?
C3 C4B 1.351(9) . ?
C7 C8 1.521(4) . ?
C9 C10 1.396(4) . ?
C9 C14 1.410(4) . ?
C9 B1 1.630(4) . ?
C10 C11 1.383(5) . ?
C11 C12 1.365(6) . ?
C12 C13 1.376(6) . ?
C13 C14 1.380(4) . ?
F2A C4A 1.351(12) . ?
F3A C5A 1.360(9) . ?
C4A C5A 1.385(10) . ?
C5A C6A 1.381(10) . ?
F2B C4B 1.345(17) . ?
F3B C5B 1.365(14) . ?
C4B C5B 1.373(15) . ?
C5B C6B 1.364(14) . ?

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
Cl6 C2S Cl8 111.1(12) . . ?
Cl7 C2S Cl6 102.9(12) . . ?
Cl7 C2S Cl8 124.1(17) . . ?
Cl1 C1S Cl2 106.7(4) . . ?
Cl3 C1S Cl1 118.6(4) . . ?
Cl3 C1S Cl2 109.2(3) . . ?
Cl4 C1S Cl5 104.5(5) . . ?
C27 N3 B2 116.1(2) . . ?
C16 C15 B2 124.8(2) . . ?
C20 C15 C16 117.6(2) . . ?
C20 C15 B2 117.6(2) . . ?
C17 C16 C15 120.2(3) . . ?
F7 C17 C16 119.9(3) . . ?
F7 C17 C18 118.1(3) . . ?
C18 C17 C16 122.0(3) . . ?
F8 C18 C17 121.4(3) . . ?
F8 C18 C19 120.7(3) . . ?
C17 C18 C19 118.0(3) . . ?
F9 C19 C18 117.3(3) . . ?
F9 C19 C20 121.0(3) . . ?
C18 C19 C20 121.7(3) . . ?
C19 C20 C15 120.5(3) . . ?
C22 C21 B2 120.4(3) . . ?
C26 C21 C22 117.5(3) . . ?
C26 C21 B2 122.1(3) . . ?
C23 C22 C21 120.3(3) . . ?
F10 C23 C22 119.9(4) . . ?
F10 C23 C24 118.2(3) . . ?
C24 C23 C22 121.9(3) . . ?
F11 C24 C23 120.3(4) . . ?
F11 C24 C25 121.1(4) . . ?
C23 C24 C25 118.5(3) . . ?
F12 C25 C24 118.1(3) . . ?
F12 C25 C26 120.2(4) . . ?
C24 C25 C26 121.7(3) . . ?
C25 C26 C21 120.1(3) . . ?
N3 C27 C28 111.8(2) . . ?
N4 C28 C27 112.9(2) . . ?
O2 B2 N3 105.7(2) . . ?
O2 B2 C15 110.6(2) . . ?
O2 B2 C21 115.4(2) . . ?
C15 B2 N3 106.5(2) . . ?
C21 B2 N3 107.6(2) . . ?
C21 B2 C15 110.5(2) . . ?
C7 N1 B1 116.8(2) . . ?
C2 C1 B1 118.2(2) . . ?
C2 C1 C6B 116.1(4) . . ?
C6A C1 C2 116.8(3) . . ?
C6A C1 B1 124.5(3) . . ?
C6B C1 B1 124.8(4) . . ?
C3 C2 C1 120.9(3) . . ?
F1 C3 C2 120.5(3) . . ?
F1 C3 C4A 117.6(4) . . ?
C2 C3 C4A 121.8(4) . . ?
C4B C3 F1 116.8(5) . . ?
C4B C3 C2 121.9(5) . . ?
N1 C7 C8 112.3(2) . . ?
N2 C8 C7 112.4(2) . . ?
C10 C9 C14 117.1(3) . . ?
C10 C9 B1 121.9(3) . . ?
C14 C9 B1 120.9(3) . . ?
C11 C10 C9 120.7(3) . . ?
F4 C11 C10 120.2(4) . . ?
F4 C11 C12 118.0(3) . . ?
C12 C11 C10 121.8(3) . . ?
F5 C12 C11 120.5(4) . . ?
F5 C12 C13 121.1(4) . . ?
C11 C12 C13 118.4(3) . . ?
F6 C13 C12 118.5(3) . . ?
F6 C13 C14 120.0(4) . . ?
C12 C13 C14 121.4(3) . . ?
C13 C14 C9 120.5(3) . . ?
O1 B1 N1 105.8(2) . . ?
O1 B1 C1 111.1(2) . . ?
O1 B1 C9 114.9(2) . . ?
C1 B1 N1 106.1(2) . . ?
C1 B1 C9 111.1(2) . . ?
C9 B1 N1 107.3(2) . . ?
F2A C4A C3 122.8(15) . . ?
F2A C4A C5A 119.5(16) . . ?
C5A C4A C3 117.6(6) . . ?
F3A C5A C4A 118.2(8) . . ?
F3A C5A C6A 120.3(8) . . ?
C6A C5A C4A 121.4(8) . . ?
C5A C6A C1 121.0(5) . . ?
C3 C4B C5B 117.3(9) . . ?
F2B C4B C3 120(2) . . ?
F2B C4B C5B 123(2) . . ?
F3B C5B C4B 117.2(11) . . ?
C6B C5B F3B 119.3(11) . . ?
C6B C5B C4B 123.2(11) . . ?
C5B C6B C1 119.4(8) . . ?

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
C1S D1 F12 1.00 2.37 3.185(7) 138.1 1_455
O2 H2C N4 0.75(5) 2.17(5) 2.900(3) 164(4) 2_565
N3 H3A O1 0.87(3) 1.99(3) 2.830(3) 162(3) .
N4 H4B F7 0.80(6) 2.38(6) 2.958(3) 130(5) 1_545
O1 H1 N2 0.93(5) 1.94(5) 2.862(3) 170(5) 2_574
N1 H1A O2 0.89(5) 1.97(5) 2.852(3) 173(4) .
N1 H1B F1 0.83(4) 2.58(4) 3.089(3) 121(3) 2_565
C7 H7A F10 0.99 2.53 3.167(3) 122.2 1_455

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.61(10)
2 0.39(10)

####################################################################### 
# 
# 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_10a_15srv091
_database_code_depnum_ccdc_archive 'CCDC 1551620'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2015-03-31
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;

_chemical_name_common            ?
_chemical_name_systematic        
' 3,4,5-Trifluorophenylboroxine -- benzylamine complex '
_chemical_formula_moiety         'C25 H15 B3 F9 N O3'
_chemical_formula_sum            'C25 H15 B3 F9 N O3'
_chemical_formula_weight         580.81
_chemical_melting_point          479(1)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3720(5)
_cell_length_b                   11.1795(5)
_cell_length_c                   12.3123(6)
_cell_angle_alpha                106.5448(14)
_cell_angle_beta                 111.4917(14)
_cell_angle_gamma                96.8493(15)
_cell_volume                     1232.74(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9217
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.12
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0750 before and 0.0378 after correction.
The Ratio of minimum to maximum transmission is 0.9701.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0990
0.00 0.00 1.00 0.0850
-2.00 2.00 1.00 0.0840
0.00 1.00 -1.00 0.1000
0.00 -1.00 1.00 0.0880
1.00 1.00 -2.00 0.1080
1.00 0.00 -1.00 0.1050
-1.00 0.00 1.00 0.0920
-2.00 1.00 0.00 0.0990
2.00 -1.00 0.00 0.1180
2.00 -1.00 -1.00 0.1000
2.00 0.00 -1.00 0.1150
-2.00 2.00 -1.00 0.0870
0.00 -2.00 -1.00 0.1600
1.00 0.00 -2.00 0.0970
0.00 2.00 -1.00 0.1250

_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 Data collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of narrow-frame ω-scans (scan 
width 0.5°, 10s exposure), every run at a different φ angle.
One run of φ-scans (scan width 1°, 1s exposure) was used for 
scaling overflowing intensities. Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27452
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         30.119
_diffrn_reflns_theta_min         2.180
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6223
_reflns_number_total             7267
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0054(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         7267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.034
_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)+(0.0490P)²+0.4680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1003
_refine_special_details          
;
 Amino H atoms - refall, other H atoms - riding model (constr)
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C8(H8), C12(H12), C14(H14), C18(H18), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.05535(9) 0.30024(8) 0.74980(7) 0.03254(18) Uani 1 1 d . . . . .
F2 F 0.09409(8) 0.55845(7) 0.82722(6) 0.02758(16) Uani 1 1 d . . . . .
F3 F 0.18335(8) 0.69424(6) 0.70887(7) 0.02490(15) Uani 1 1 d . . . . .
F4 F 0.13661(8) 0.67065(7) 0.07296(7) 0.02614(16) Uani 1 1 d . . . . .
F5 F 0.37277(8) 0.71619(8) 0.02962(7) 0.03052(17) Uani 1 1 d . . . . .
F6 F 0.59218(8) 0.61493(9) 0.12185(8) 0.03329(19) Uani 1 1 d . . . . .
F7 F 0.82316(8) 0.06711(8) 0.36471(8) 0.03233(18) Uani 1 1 d . . . . .
F8 F 0.88830(7) 0.02064(7) 0.57816(8) 0.02930(17) Uani 1 1 d . . . . .
F9 F 0.73125(8) 0.07663(8) 0.71143(7) 0.03067(17) Uani 1 1 d . . . . .
O1 O 0.22367(8) 0.38538(7) 0.34033(7) 0.01451(14) Uani 1 1 d . . . . .
O2 O 0.44626(8) 0.34003(8) 0.35271(7) 0.01824(15) Uani 1 1 d . . . . .
O3 O 0.31740(7) 0.23529(7) 0.43992(7) 0.01471(14) Uani 1 1 d . . . . .
N N 0.06059(9) 0.18549(8) 0.30460(8) 0.01349(16) Uani 1 1 d . . . . .
H1N H 0.0485(16) 0.1287(15) 0.3366(14) 0.023(4) Uiso 1 1 d . . . . .
H2N H -0.0177(17) 0.2150(15) 0.2936(14) 0.027(4) Uiso 1 1 d . . . . .
C1 C 0.16869(10) 0.37038(9) 0.52173(9) 0.01341(17) Uani 1 1 d . . . . .
C2 C 0.12499(12) 0.30157(10) 0.58670(10) 0.01799(19) Uani 1 1 d . . . . .
H2 H 0.1132 0.2109 0.5611 0.022 Uiso 1 1 calc R . . . .
C3 C 0.09910(12) 0.36495(11) 0.68741(10) 0.0201(2) Uani 1 1 d . . . . .
C4 C 0.11813(11) 0.49692(11) 0.72839(10) 0.0185(2) Uani 1 1 d . . . . .
C5 C 0.16290(10) 0.56422(10) 0.66542(10) 0.01656(19) Uani 1 1 d . . . . .
C6 C 0.18674(10) 0.50397(10) 0.56273(9) 0.01490(18) Uani 1 1 d . . . . .
H6 H 0.2153 0.5529 0.5200 0.018 Uiso 1 1 calc R . . . .
C7 C 0.35077(10) 0.49021(9) 0.23885(9) 0.01433(18) Uani 1 1 d . . . . .
C8 C 0.23670(11) 0.54296(10) 0.18952(9) 0.01590(18) Uani 1 1 d . . . . .
H8 H 0.1536 0.5267 0.2040 0.019 Uiso 1 1 calc R . . . .
C9 C 0.24482(11) 0.61828(10) 0.12003(10) 0.01736(19) Uani 1 1 d . . . . .
C10 C 0.36477(12) 0.64300(11) 0.09740(10) 0.0198(2) Uani 1 1 d . . . . .
C11 C 0.47714(11) 0.59083(11) 0.14626(11) 0.0206(2) Uani 1 1 d . . . . .
C12 C 0.47210(11) 0.51531(10) 0.21628(10) 0.01772(19) Uani 1 1 d . . . . .
H12 H 0.5506 0.4804 0.2491 0.021 Uiso 1 1 calc R . . . .
C13 C 0.55568(10) 0.18973(9) 0.45864(9) 0.01515(18) Uani 1 1 d . . . . .
C14 C 0.63642(11) 0.15894(10) 0.39019(10) 0.0186(2) Uani 1 1 d . . . . .
H14 H 0.6165 0.1784 0.3164 0.022 Uiso 1 1 calc R . . . .
C15 C 0.74500(11) 0.10019(11) 0.43022(11) 0.0208(2) Uani 1 1 d . . . . .
C16 C 0.77825(11) 0.07390(10) 0.53888(11) 0.0203(2) Uani 1 1 d . . . . .
C17 C 0.69808(12) 0.10392(10) 0.60626(10) 0.0195(2) Uani 1 1 d . . . . .
C18 C 0.58654(11) 0.15995(10) 0.56692(10) 0.01720(19) Uani 1 1 d . . . . .
H18 H 0.5309 0.1783 0.6132 0.021 Uiso 1 1 calc R . . . .
C19 C 0.05553(11) 0.11908(10) 0.17833(9) 0.0183(2) Uani 1 1 d . . . . .
H19A H 0.1339 0.0748 0.1868 0.022 Uiso 1 1 calc R . . . .
H19B H 0.0692 0.1835 0.1400 0.022 Uiso 1 1 calc R . . . .
C20 C -0.08629(11) 0.02250(10) 0.09598(9) 0.01594(19) Uani 1 1 d . . . . .
C21 C -0.10510(13) -0.10401(11) 0.09277(10) 0.0213(2) Uani 1 1 d . . . . .
H21 H -0.0261 -0.1315 0.1384 0.026 Uiso 1 1 calc R . . . .
C22 C -0.23903(14) -0.19022(12) 0.02304(11) 0.0276(2) Uani 1 1 d . . . . .
H22 H -0.2516 -0.2764 0.0213 0.033 Uiso 1 1 calc R . . . .
C23 C -0.35430(13) -0.15041(13) -0.04392(12) 0.0310(3) Uani 1 1 d . . . . .
H23 H -0.4460 -0.2092 -0.0911 0.037 Uiso 1 1 calc R . . . .
C24 C -0.33588(13) -0.02495(13) -0.04208(12) 0.0310(3) Uani 1 1 d . . . . .
H24 H -0.4148 0.0021 -0.0884 0.037 Uiso 1 1 calc R . . . .
C25 C -0.20198(12) 0.06130(11) 0.02748(11) 0.0233(2) Uani 1 1 d . . . . .
H25 H -0.1895 0.1471 0.0282 0.028 Uiso 1 1 calc R . . . .
B1 B 0.20218(11) 0.29962(10) 0.40495(10) 0.01291(19) Uani 1 1 d . . . . .
B2 B 0.33838(12) 0.40152(10) 0.31451(10) 0.0143(2) Uani 1 1 d . . . . .
B3 B 0.43215(12) 0.25759(11) 0.41550(10) 0.0144(2) 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 C3 1.3464(12) . ?
F2 C4 1.3425(12) . ?
F3 C5 1.3580(12) . ?
F4 C9 1.3460(12) . ?
F5 C10 1.3401(12) . ?
F6 C11 1.3486(12) . ?
F7 C15 1.3509(13) . ?
F8 C16 1.3464(11) . ?
F9 C17 1.3461(12) . ?
O1 B1 1.4544(12) . ?
O1 B2 1.3446(13) . ?
O2 B2 1.3885(13) . ?
O2 B3 1.3874(13) . ?
O3 B1 1.4612(12) . ?
O3 B3 1.3428(13) . ?
N C19 1.4982(13) . ?
N B1 1.6239(14) . ?
C1 C2 1.4036(14) . ?
C1 C6 1.3983(13) . ?
C1 B1 1.6117(14) . ?
C2 C3 1.3786(15) . ?
C3 C4 1.3798(16) . ?
C4 C5 1.3768(15) . ?
C5 C6 1.3774(14) . ?
C7 C8 1.4000(13) . ?
C7 C12 1.3986(14) . ?
C7 B2 1.5655(14) . ?
C8 C9 1.3764(14) . ?
C9 C10 1.3848(15) . ?
C10 C11 1.3815(15) . ?
C11 C12 1.3769(14) . ?
C13 C14 1.3968(14) . ?
C13 C18 1.3986(14) . ?
C13 B3 1.5690(14) . ?
C14 C15 1.3772(14) . ?
C15 C16 1.3803(16) . ?
C16 C17 1.3805(16) . ?
C17 C18 1.3785(14) . ?
C19 C20 1.5041(14) . ?
C20 C21 1.3917(15) . ?
C20 C25 1.3893(15) . ?
C21 C22 1.3897(16) . ?
C22 C23 1.3859(19) . ?
C23 C24 1.385(2) . ?
C24 C25 1.3895(17) . ?

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
B2 O1 B1 122.50(8) . . ?
B3 O2 B2 118.78(8) . . ?
B3 O3 B1 121.73(8) . . ?
C19 N B1 117.43(8) . . ?
C2 C1 B1 121.60(9) . . ?
C6 C1 C2 118.38(9) . . ?
C6 C1 B1 120.00(8) . . ?
C3 C2 C1 120.33(10) . . ?
F1 C3 C2 121.11(10) . . ?
F1 C3 C4 117.68(10) . . ?
C2 C3 C4 121.21(10) . . ?
F2 C4 C3 121.04(10) . . ?
F2 C4 C5 120.71(10) . . ?
C5 C4 C3 118.24(9) . . ?
F3 C5 C4 117.16(9) . . ?
F3 C5 C6 120.63(9) . . ?
C4 C5 C6 122.21(9) . . ?
C5 C6 C1 119.60(9) . . ?
C8 C7 B2 119.58(9) . . ?
C12 C7 C8 118.98(9) . . ?
C12 C7 B2 121.41(9) . . ?
C9 C8 C7 120.11(9) . . ?
F4 C9 C8 120.81(9) . . ?
F4 C9 C10 118.22(9) . . ?
C8 C9 C10 120.97(9) . . ?
F5 C10 C9 121.04(10) . . ?
F5 C10 C11 120.20(10) . . ?
C11 C10 C9 118.76(9) . . ?
F6 C11 C10 117.74(9) . . ?
F6 C11 C12 120.71(10) . . ?
C12 C11 C10 121.54(10) . . ?
C11 C12 C7 119.64(9) . . ?
C14 C13 C18 119.23(9) . . ?
C14 C13 B3 120.66(9) . . ?
C18 C13 B3 120.11(9) . . ?
C15 C14 C13 119.69(10) . . ?
F7 C15 C14 121.03(10) . . ?
F7 C15 C16 117.78(10) . . ?
C14 C15 C16 121.19(10) . . ?
F8 C16 C15 119.91(10) . . ?
F8 C16 C17 121.01(10) . . ?
C15 C16 C17 119.07(9) . . ?
F9 C17 C16 118.26(9) . . ?
F9 C17 C18 120.70(10) . . ?
C18 C17 C16 121.04(10) . . ?
C17 C18 C13 119.74(10) . . ?
N C19 C20 109.94(8) . . ?
C21 C20 C19 120.63(10) . . ?
C25 C20 C19 119.82(10) . . ?
C25 C20 C21 119.46(10) . . ?
C22 C21 C20 120.21(11) . . ?
C23 C22 C21 120.00(11) . . ?
C24 C23 C22 120.04(11) . . ?
C23 C24 C25 120.02(12) . . ?
C20 C25 C24 120.27(11) . . ?
O1 B1 O3 113.59(8) . . ?
O1 B1 N 105.84(8) . . ?
O1 B1 C1 111.96(8) . . ?
O3 B1 N 105.59(8) . . ?
O3 B1 C1 112.07(8) . . ?
C1 B1 N 107.18(7) . . ?
O1 B2 O2 121.31(9) . . ?
O1 B2 C7 119.71(9) . . ?
O2 B2 C7 118.98(9) . . ?
O2 B3 C13 118.00(9) . . ?
O3 B3 O2 122.03(9) . . ?
O3 B3 C13 119.97(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N H1N F7 0.857(16) 2.530(15) 3.0790(11) 122.7(12) 1_455
N H1N F8 0.857(16) 2.252(16) 3.0497(11) 154.9(14) 2_656
N H2N F3 0.892(16) 2.092(16) 2.9779(11) 172.0(14) 2_566

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# 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_7a_16srv413
_database_code_depnum_ccdc_archive 'CCDC 1563950'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2016-11-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;

_chemical_name_common            ?
_chemical_name_systematic        3,4,5-trifluorophenylboroxine
_chemical_formula_moiety         'C18 H6 B3 F9 O3'
_chemical_formula_sum            'C18 H6 B3 F9 O3'
_chemical_formula_weight         473.66
_chemical_melting_point          ?
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   17.083(4)
_cell_length_b                   13.093(3)
_cell_length_c                   7.990(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1787.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7348
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.51
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1096 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.8873.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22891
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         2.385
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1466
_reflns_number_total             2162
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.049
_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)+(0.0600P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1170
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.33544(7) 0.35130(7) 0.46045(15) 0.0326(3) Uani 1 1 d . . . . .
F2 F 0.22161(6) 0.44746(9) 0.29114(15) 0.0335(3) Uani 1 1 d . . . . .
F3 F 0.21638(6) 0.65261(8) 0.27961(14) 0.0327(3) Uani 1 1 d . . . . .
F4 F 0.39036(7) 1.16468(8) 0.57511(16) 0.0369(3) Uani 1 1 d . . . . .
F5 F 0.5000 1.26713(11) 0.7500 0.0348(4) Uani 1 2 d S T P . .
O1 O 0.44870(6) 0.78147(8) 0.64872(14) 0.0178(3) Uani 1 1 d . . . . .
O2 O 0.5000 0.62463(13) 0.7500 0.0183(4) Uani 1 2 d S T P . .
C1 C 0.38609(10) 0.61550(13) 0.5480(2) 0.0170(4) Uani 1 1 d . . . . .
C2 C 0.38885(10) 0.50893(13) 0.5496(2) 0.0186(4) Uani 1 1 d . . . . .
C3 C 0.33357(10) 0.45441(13) 0.4628(2) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.27511(10) 0.50259(14) 0.3749(2) 0.0219(4) Uani 1 1 d . . . . .
C5 C 0.27302(10) 0.60771(14) 0.3709(2) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.32735(11) 0.66504(14) 0.4567(2) 0.0194(4) Uani 1 1 d . . . . .
C7 C 0.5000 0.95231(17) 0.7500 0.0166(5) Uani 1 2 d S T P . .
C8 C 0.44291(11) 1.00589(13) 0.6615(2) 0.0194(4) Uani 1 1 d . . . . .
C9 C 0.44401(10) 1.11117(14) 0.6623(2) 0.0221(4) Uani 1 1 d . . . . .
C10 C 0.5000 1.16430(18) 0.7500 0.0238(6) Uani 1 2 d S T P . .
B1 B 0.44702(11) 0.67698(15) 0.6521(2) 0.0172(4) Uani 1 1 d . . . . .
B2 B 0.5000 0.8344(2) 0.7500 0.0152(6) Uani 1 2 d S T P . .
H2 H 0.4302(12) 0.4749(15) 0.609(2) 0.029(5) Uiso 1 1 d . . . . .
H8 H 0.4018(10) 0.9701(13) 0.600(2) 0.013(4) Uiso 1 1 d . . . . .
H6 H 0.3262(11) 0.7341(16) 0.451(2) 0.025(5) Uiso 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 C3 1.350(2) . ?
F2 C4 1.3432(19) . ?
F3 C5 1.3468(19) . ?
F4 C9 1.348(2) . ?
F5 C10 1.346(3) . ?
O1 B1 1.369(2) . ?
O1 B2 1.3797(18) . ?
O2 B1 1.379(2) 4_656 ?
O2 B1 1.379(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.400(2) . ?
C1 B1 1.556(3) . ?
C2 C3 1.372(2) . ?
C2 H2 0.96(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.377(3) . ?
C5 C6 1.377(2) . ?
C6 H6 0.91(2) . ?
C7 C8 1.394(2) 4_656 ?
C7 C8 1.394(2) . ?
C7 B2 1.544(3) . ?
C8 C9 1.379(2) . ?
C8 H8 0.979(18) . ?
C9 C10 1.375(2) . ?
C10 C9 1.375(2) 4_656 ?
B2 O1 1.3797(18) 4_656 ?

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 B2 120.26(15) . . ?
B1 O2 B1 120.4(2) 4_656 . ?
C2 C1 C6 119.47(16) . . ?
C2 C1 B1 119.31(15) . . ?
C6 C1 B1 121.20(16) . . ?
C1 C2 H2 119.5(12) . . ?
C3 C2 C1 119.49(16) . . ?
C3 C2 H2 121.0(12) . . ?
F1 C3 C2 120.72(16) . . ?
F1 C3 C4 117.97(15) . . ?
C2 C3 C4 121.31(16) . . ?
F2 C4 C3 120.15(16) . . ?
F2 C4 C5 120.52(16) . . ?
C3 C4 C5 119.31(16) . . ?
F3 C5 C4 117.87(16) . . ?
F3 C5 C6 121.06(16) . . ?
C6 C5 C4 121.06(16) . . ?
C1 C6 H6 120.3(13) . . ?
C5 C6 C1 119.35(17) . . ?
C5 C6 H6 120.4(13) . . ?
C8 C7 C8 119.6(2) 4_656 . ?
C8 C7 B2 120.22(11) . . ?
C8 C7 B2 120.22(11) 4_656 . ?
C7 C8 H8 121.1(10) . . ?
C9 C8 C7 119.44(18) . . ?
C9 C8 H8 119.4(10) . . ?
F4 C9 C8 120.55(17) . . ?
F4 C9 C10 118.27(17) . . ?
C10 C9 C8 121.17(18) . . ?
F5 C10 C9 120.39(11) . . ?
F5 C10 C9 120.40(12) . 4_656 ?
C9 C10 C9 119.2(2) . 4_656 ?
O1 B1 O2 119.64(16) . . ?
O1 B1 C1 121.36(16) . . ?
O2 B1 C1 119.00(16) . . ?
O1 B2 O1 119.7(2) . 4_656 ?
O1 B2 C7 120.16(11) . . ?
O1 B2 C7 120.16(11) 4_656 . ?

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
C2 C1 B1 O1 177.16(16) . . . . ?
C2 C1 B1 O2 -3.1(2) . . . . ?
C6 C1 B1 O1 -4.6(3) . . . . ?
C6 C1 B1 O2 175.11(15) . . . . ?
C8 C7 B2 O1 -173.22(10) 4_656 . . . ?
C8 C7 B2 O1 -173.22(10) . . . 4_656 ?
C8 C7 B2 O1 6.78(10) 4_656 . . 4_656 ?
C8 C7 B2 O1 6.78(10) . . . . ?
B1 O1 B2 O1 1.91(11) . . . 4_656 ?
B1 O1 B2 C7 -178.09(11) . . . . ?
B1 O2 B1 O1 1.89(11) 4_656 . . . ?
B1 O2 B1 C1 -177.84(18) 4_656 . . . ?
B2 O1 B1 O2 -3.8(2) . . . . ?
B2 O1 B1 C1 175.94(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform, pentane'
####################################################################### 
# 
# 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_10d_16srv262
_database_code_depnum_ccdc_archive 'CCDC 1551622'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2017-02-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7

_chemical_name_common            ?
_chemical_name_systematic        
'phenylboroxine complex with 4 equiv. benzylamine '
_chemical_formula_moiety         'C32 H33 B3 N2 O3, 2(C7 H9 N)'
_chemical_formula_sum            'C46 H51 B3 N4 O3'
_chemical_formula_weight         740.33
_chemical_melting_point          329.4(3)
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   21.2120(9)
_cell_length_b                   11.2705(5)
_cell_length_c                   18.8494(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.8857(16)
_cell_angle_gamma                90
_cell_volume                     4087.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.839
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker, 2014) was used for absorption correction.
wR2(int) was 0.1307 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.9421.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 2.00 1.00 0.0730
0.00 -2.00 -1.00 0.0670
-1.00 0.00 2.00 0.1330
1.00 0.00 -2.00 0.0920
-1.00 -2.00 1.00 0.0920
-1.00 0.00 0.00 0.0640
1.00 0.00 0.00 0.0490
1.00 -1.00 -2.00 0.0990
-1.00 2.00 2.00 0.0940

_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.128
_exptl_special_details           
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of 340 narrow-frame ω-scans (scan 
width 0.5°, 10s exposure), every run at a different φ angle.
Two runs of 358 φ-scans (scan width 1°, 1.5s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            68095
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.998
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.117
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  D8V
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6020
_reflns_number_total             8022
_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.bruker_data_scaling   'SADABS V2014/5 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v.2016.1_0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         8022
_refine_ls_number_restraints     604
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.030
_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)+(0.0380P)²+2.5270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1169
_refine_special_details          
; Amino H atoms: refall, other H atoms: riding model (constr).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2-C3B \\sim C2-C7B \\sim C4B-C3B \\sim C4A-C3A \\sim C5A-C4A \\sim C5B-C4B
\\sim C6B-C5B \\sim C6A-C5A ~
 C7A-C6A \\sim C7B-C6B \\sim C2-C3A \\sim C2-C7A
 with sigma of 0.02
 C40B-C35B \\sim C40A-C35A \\sim C40B-C39B \\sim C40A-C39A \\sim C39B-C38B
\\sim C39A-C38A \\sim C38B-
 C37B \\sim C38A-C37A \\sim C37A-C36A \\sim C37B-C36B \\sim C36B-C35B \\sim
C36A-C35A
 with sigma of 0.02
 C35B-C34 \\sim C35A-C34
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C35B) = Uanis(C35A)
Uanis(C7A) = Uanis(C7B)
Uanis(C6A) = Uanis(C6B)
Uanis(C5A) = Uanis(C5B)
Uanis(C4A) = Uanis(C4B)
Uanis(C3A) = Uanis(C3B)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C3A(0.5) H3A(0.5) C4A(0.5) H4A(0.5) C5A(0.5) H5A(0.5) C6A(0.5)
 H6A(0.5) C7A(0.5) H7A(0.5) C3B(0.5) H3B(0.5) C4B(0.5) H4B(0.5) C5B(0.5)
 H5B(0.5) C6B(0.5) H6B(0.5) C7B(0.5) H7B(0.5) C35A(0.7) C36A(0.7) H36A(0.7)
 C37A(0.7) H37A(0.7) C38A(0.7) H38A(0.7) C39A(0.7) H39A(0.7) C40A(0.7)
 H40A(0.7) C35B(0.3) C36B(0.3) H36B(0.3) C37B(0.3) H37B(0.3) C38B(0.3)
 H38B(0.3) C39B(0.3) H39B(0.3) C40B(0.3) H40B(0.3)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C14(H14A,H14B), C41(H41A,H41B)
6.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C3B(H3B), C4B(H4B),
 C5B(H5B), C6B(H6B), C7B(H7B), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
 C36A(H36A), C37A(H37A), C38A(H38A), C39A(H39A), C40A(H40A), C36B(H36B),
 C37B(H37B), C38B(H38B), C39B(H39B), C40B(H40B), C43(H43), C44(H44), C45(H45),
 C46(H46), C47(H47)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22959(6) 0.75175(11) 0.51854(6) 0.0277(3) Uani 1 1 d . U . . .
O2 O 0.27823(6) 0.92207(11) 0.47857(6) 0.0244(3) Uani 1 1 d . U . . .
O3 O 0.23307(6) 0.75934(10) 0.39101(6) 0.0234(3) Uani 1 1 d . U . . .
N1 N 0.12495(8) 0.70955(17) 0.40085(9) 0.0302(4) Uani 1 1 d . U . . .
H1A H 0.1056(11) 0.6751(19) 0.4317(13) 0.046(6) Uiso 1 1 d . . . . .
H1B H 0.1145(11) 0.791(2) 0.3991(13) 0.049(7) Uiso 1 1 d . . . . .
N2 N 0.35618(7) 0.79398(14) 0.58411(8) 0.0232(3) Uani 1 1 d . U . . .
H2A H 0.3604(9) 0.7537(17) 0.5442(11) 0.031(5) Uiso 1 1 d . . . . .
H2B H 0.3900(10) 0.8533(18) 0.5997(11) 0.036(5) Uiso 1 1 d . . . . .
C1 C 0.09115(9) 0.6620(2) 0.31985(11) 0.0392(5) Uani 1 1 d . U . . .
H1C H 0.1059 0.5787 0.3197 0.047 Uiso 1 1 calc R . . . .
H1D H 0.1069 0.7084 0.2857 0.047 Uiso 1 1 calc R . . . .
C3A C -0.0143(4) 0.5751(13) 0.3151(10) 0.0504(14) Uani 0.5 1 d D U P A 1
H3A H 0.0157 0.5171 0.3493 0.061 Uiso 0.5 1 calc R . P A 1
C4A C -0.0851(4) 0.5683(8) 0.2930(5) 0.0637(15) Uani 0.5 1 d D U P A 1
H4A H -0.1044 0.5041 0.3100 0.076 Uiso 0.5 1 calc R . P A 1
C5A C -0.1269(3) 0.6554(6) 0.2464(4) 0.0504(13) Uani 0.5 1 d D U P A 1
H5A H -0.1754 0.6522 0.2323 0.061 Uiso 0.5 1 calc R . P A 1
C6A C -0.1005(4) 0.7479(7) 0.2194(5) 0.0444(13) Uani 0.5 1 d D U P A 1
H6A H -0.1310 0.8057 0.1854 0.053 Uiso 0.5 1 calc R . P A 1
C7A C -0.0283(6) 0.7565(15) 0.2421(10) 0.0398(19) Uani 0.5 1 d D U P A 1
H7A H -0.0090 0.8223 0.2267 0.048 Uiso 0.5 1 calc R . P A 1
C3B C -0.0298(4) 0.5884(13) 0.3014(10) 0.0504(14) Uani 0.5 1 d D U P A 2
H3B H -0.0098 0.5232 0.3355 0.061 Uiso 0.5 1 calc R . P A 2
C4B C -0.1001(4) 0.6011(8) 0.2679(5) 0.0637(15) Uani 0.5 1 d D U P A 2
H4B H -0.1281 0.5466 0.2803 0.076 Uiso 0.5 1 calc R . P A 2
C5B C -0.1311(3) 0.6924(6) 0.2162(4) 0.0504(13) Uani 0.5 1 d D U P A 2
H5B H -0.1803 0.6997 0.1926 0.061 Uiso 0.5 1 calc R . P A 2
C6B C -0.0908(4) 0.7737(8) 0.1985(5) 0.0444(13) Uani 0.5 1 d D U P A 2
H6B H -0.1113 0.8389 0.1646 0.053 Uiso 0.5 1 calc R . P A 2
C7B C -0.0182(6) 0.7561(15) 0.2326(11) 0.0398(19) Uani 0.5 1 d D U P A 2
H7B H 0.0101 0.8066 0.2178 0.048 Uiso 0.5 1 calc R . P A 2
C8 C 0.22859(8) 0.55644(16) 0.45025(9) 0.0237(4) Uani 1 1 d . U . . .
C9 C 0.20624(10) 0.47845(18) 0.49271(10) 0.0341(5) Uani 1 1 d . U . . .
H9 H 0.1781 0.5084 0.5167 0.041 Uiso 1 1 calc R . . . .
C10 C 0.22362(12) 0.35925(19) 0.50115(12) 0.0434(5) Uani 1 1 d . U . . .
H10 H 0.2076 0.3092 0.5306 0.052 Uiso 1 1 calc R . . . .
C11 C 0.26423(12) 0.31309(19) 0.46682(12) 0.0434(5) Uani 1 1 d . U . . .
H11 H 0.2763 0.2313 0.4723 0.052 Uiso 1 1 calc R . . . .
C12 C 0.28704(11) 0.38703(18) 0.42453(12) 0.0388(5) Uani 1 1 d . U . . .
H12 H 0.3151 0.3563 0.4006 0.047 Uiso 1 1 calc R . . . .
C13 C 0.26931(9) 0.50635(17) 0.41658(10) 0.0283(4) Uani 1 1 d . U . . .
H13 H 0.2856 0.5557 0.3870 0.034 Uiso 1 1 calc R . . . .
C14 C 0.36971(10) 0.70845(17) 0.64888(10) 0.0314(4) Uani 1 1 d . U . . .
H14A H 0.3305 0.6517 0.6331 0.038 Uiso 1 1 calc R . . . .
H14B H 0.3717 0.7522 0.6953 0.038 Uiso 1 1 calc R . . . .
C15 C 0.43617(9) 0.64035(16) 0.67077(10) 0.0265(4) Uani 1 1 d . U . . .
C16 C 0.43563(10) 0.52636(17) 0.64249(10) 0.0299(4) Uani 1 1 d . U . . .
H16 H 0.3927 0.4900 0.6102 0.036 Uiso 1 1 calc R . . . .
C17 C 0.49715(11) 0.46523(18) 0.66100(11) 0.0372(5) Uani 1 1 d . U . . .
H17 H 0.4962 0.3874 0.6412 0.045 Uiso 1 1 calc R . . . .
C18 C 0.55990(11) 0.5171(2) 0.70815(12) 0.0412(5) Uani 1 1 d . U . . .
H18 H 0.6021 0.4753 0.7206 0.049 Uiso 1 1 calc R . . . .
C19 C 0.56094(10) 0.6294(2) 0.73690(12) 0.0413(5) Uani 1 1 d . U . . .
H19 H 0.6041 0.6649 0.7696 0.050 Uiso 1 1 calc R . . . .
C20 C 0.49989(10) 0.69100(18) 0.71873(10) 0.0337(4) Uani 1 1 d . U . . .
H20 H 0.5013 0.7686 0.7391 0.040 Uiso 1 1 calc R . . . .
C21 C 0.26231(8) 0.93086(16) 0.60577(9) 0.0225(4) Uani 1 1 d . U . . .
C22 C 0.24330(11) 0.8784(2) 0.66070(12) 0.0425(5) Uani 1 1 d . U . . .
H22 H 0.2405 0.7943 0.6618 0.051 Uiso 1 1 calc R . . . .
C23 C 0.22834(12) 0.9438(2) 0.71380(13) 0.0494(6) Uani 1 1 d . U . . .
H23 H 0.2165 0.9046 0.7511 0.059 Uiso 1 1 calc R . . . .
C24 C 0.23072(9) 1.0663(2) 0.71243(11) 0.0369(5) Uani 1 1 d . U . . .
H24 H 0.2195 1.1120 0.7479 0.044 Uiso 1 1 calc R . . . .
C25 C 0.24954(10) 1.12122(18) 0.65901(11) 0.0366(5) Uani 1 1 d . U . . .
H25 H 0.2515 1.2053 0.6576 0.044 Uiso 1 1 calc R . . . .
C26 C 0.26564(9) 1.05369(17) 0.60715(10) 0.0291(4) Uani 1 1 d . U . . .
H26 H 0.2794 1.0931 0.5714 0.035 Uiso 1 1 calc R . . . .
C27 C 0.26854(8) 0.94273(16) 0.34036(9) 0.0248(4) Uani 1 1 d . U . . .
C28 C 0.24315(9) 0.89757(18) 0.26442(10) 0.0299(4) Uani 1 1 d . U . . .
H28 H 0.2175 0.8255 0.2525 0.036 Uiso 1 1 calc R . . . .
C29 C 0.25454(11) 0.95572(19) 0.20598(11) 0.0374(5) Uani 1 1 d . U . . .
H29 H 0.2362 0.9240 0.1545 0.045 Uiso 1 1 calc R . . . .
C30 C 0.29232(11) 1.0594(2) 0.22250(12) 0.0423(5) Uani 1 1 d . U . . .
H30 H 0.3011 1.0980 0.1828 0.051 Uiso 1 1 calc R . . . .
C31 C 0.31756(11) 1.10750(19) 0.29700(12) 0.0407(5) Uani 1 1 d . U . . .
H31 H 0.3432 1.1795 0.3085 0.049 Uiso 1 1 calc R . . . .
C32 C 0.30490(9) 1.04902(17) 0.35470(11) 0.0313(4) Uani 1 1 d . U . . .
H32 H 0.3217 1.0829 0.4055 0.038 Uiso 1 1 calc R . . . .
B1 B 0.21031(10) 0.69640(19) 0.44409(11) 0.0241(4) Uani 1 1 d . U . . .
B2 B 0.27542(10) 0.85080(19) 0.54263(11) 0.0238(4) Uani 1 1 d . U . . .
B3 B 0.25884(9) 0.87163(19) 0.40729(11) 0.0229(4) Uani 1 1 d . U . . .
N3 N 0.10168(11) 0.9643(3) 0.4106(2) 0.0669(8) Uani 1 1 d . U . . .
H3C H 0.124(2) 1.012(4) 0.409(3) 0.134(19) Uiso 1 1 d . . . . .
H3D H 0.127(2) 0.964(4) 0.468(2) 0.129(15) Uiso 1 1 d . . . . .
C34 C 0.03431(12) 0.9834(2) 0.40843(15) 0.0455(5) Uani 1 1 d D U . . .
H34A H 0.0227(16) 0.920(3) 0.4341(18) 0.096(10) Uiso 1 1 d . . . . .
H34B H -0.0001(15) 0.970(3) 0.3478(18) 0.091(10) Uiso 1 1 d . . . . .
C35A C 0.0161(4) 1.1012(7) 0.4315(5) 0.0336(8) Uani 0.7 1 d D U P B 1
C36A C -0.05225(19) 1.1354(3) 0.40394(18) 0.0416(8) Uani 0.7 1 d D U P B 1
H36A H -0.0876 1.0843 0.3698 0.050 Uiso 0.7 1 calc R . P B 1
C37A C -0.07038(19) 1.2431(3) 0.4250(2) 0.0473(9) Uani 0.7 1 d D U P B 1
H37A H -0.1179 1.2655 0.4053 0.057 Uiso 0.7 1 calc R . P B 1
C38A C -0.0200(2) 1.3177(3) 0.4742(3) 0.0396(7) Uani 0.7 1 d D U P B 1
H38A H -0.0322 1.3934 0.4867 0.048 Uiso 0.7 1 calc R . P B 1
C39A C 0.04809(19) 1.2825(3) 0.5051(3) 0.0592(11) Uani 0.7 1 d D U P B 1
H39A H 0.0831 1.3314 0.5418 0.071 Uiso 0.7 1 calc R . P B 1
C40A C 0.06556(17) 1.1747(3) 0.4824(3) 0.0508(9) Uani 0.7 1 d D U P B 1
H40A H 0.1130 1.1517 0.5027 0.061 Uiso 0.7 1 calc R . P B 1
C35B C 0.0278(10) 1.1031(18) 0.4469(12) 0.0336(8) Uani 0.3 1 d D U P B 2
C36B C -0.0310(5) 1.1759(8) 0.4048(6) 0.050(3) Uiso 0.3 1 d D U P B 2
H36B H -0.0632 1.1513 0.3542 0.060 Uiso 0.3 1 calc R . P B 2
C37B C -0.0430(6) 1.2814(9) 0.4349(6) 0.053(3) Uiso 0.3 1 d D U P B 2
H37B H -0.0837 1.3267 0.4069 0.064 Uiso 0.3 1 calc R . P B 2
C38B C 0.0064(5) 1.3194(9) 0.5075(5) 0.044(3) Uiso 0.3 1 d D U P B 2
H38B H -0.0009 1.3917 0.5290 0.053 Uiso 0.3 1 calc R . P B 2
C39B C 0.0653(4) 1.2539(7) 0.5486(5) 0.045(2) Uiso 0.3 1 d D U P B 2
H39B H 0.0989 1.2818 0.5976 0.054 Uiso 0.3 1 calc R . P B 2
C40B C 0.0757(4) 1.1481(7) 0.5187(4) 0.032(2) Uiso 0.3 1 d D U P B 2
H40B H 0.1167 1.1040 0.5477 0.038 Uiso 0.3 1 calc R . P B 2
N4 N 0.47811(9) 0.96383(16) 0.62888(11) 0.0375(4) Uani 1 1 d . U . . .
H4C H 0.4985(14) 1.007(2) 0.6812(17) 0.080(9) Uiso 1 1 d . . . . .
H4D H 0.5166(15) 0.929(3) 0.6174(17) 0.091(10) Uiso 1 1 d . . . . .
C41 C 0.44680(10) 1.05133(19) 0.56884(13) 0.0430(5) Uani 1 1 d . U . . .
H41A H 0.4083 1.0886 0.5774 0.052 Uiso 1 1 calc R . . . .
H41B H 0.4257 1.0091 0.5181 0.052 Uiso 1 1 calc R . . . .
C42 C 0.49193(9) 1.15056(17) 0.56054(11) 0.0308(4) Uani 1 1 d . U . . .
C43 C 0.46231(10) 1.22692(19) 0.49720(11) 0.0379(5) Uani 1 1 d . U . . .
H43 H 0.4154 1.2150 0.4610 0.046 Uiso 1 1 calc R . . . .
C44 C 0.49921(10) 1.31935(19) 0.48565(11) 0.0371(5) Uani 1 1 d . U . . .
H44 H 0.4779 1.3700 0.4416 0.044 Uiso 1 1 calc R . . . .
C45 C 0.56700(9) 1.33866(17) 0.53776(11) 0.0306(4) Uani 1 1 d . U . . .
H45 H 0.5925 1.4030 0.5302 0.037 Uiso 1 1 calc R . . . .
C46 C 0.59781(9) 1.26394(17) 0.60119(11) 0.0305(4) Uani 1 1 d . U . . .
H46 H 0.6447 1.2767 0.6373 0.037 Uiso 1 1 calc R . . . .
C47 C 0.56042(9) 1.16999(17) 0.61243(11) 0.0304(4) Uani 1 1 d . U . . .
H47 H 0.5820 1.1188 0.6561 0.036 Uiso 1 1 calc R . . . .
C2 C 0.01332(9) 0.66690(17) 0.28731(11) 0.0339(4) Uani 1 1 d 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 B1 1.429(2) . ?
O1 B2 1.423(2) . ?
O2 B2 1.472(2) . ?
O2 B3 1.354(2) . ?
O3 B1 1.464(2) . ?
O3 B3 1.361(2) . ?
N1 C1 1.487(2) . ?
N1 B1 1.650(2) . ?
N2 C14 1.486(2) . ?
N2 B2 1.682(2) . ?
C1 C2 1.501(2) . ?
C3A C4A 1.382(8) . ?
C3A C2 1.395(9) . ?
C4A C5A 1.366(7) . ?
C5A C6A 1.378(7) . ?
C6A C7A 1.409(9) . ?
C7A C2 1.375(9) . ?
C3B C4B 1.361(8) . ?
C3B C2 1.376(9) . ?
C4B C5B 1.379(7) . ?
C5B C6B 1.387(7) . ?
C6B C7B 1.411(9) . ?
C7B C2 1.393(9) . ?
C8 C9 1.399(2) . ?
C8 C13 1.389(2) . ?
C8 B1 1.617(3) . ?
C9 C10 1.384(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.374(3) . ?
C12 C13 1.387(3) . ?
C14 C15 1.502(3) . ?
C15 C16 1.389(3) . ?
C15 C20 1.393(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.373(3) . ?
C19 C20 1.380(3) . ?
C21 C22 1.391(2) . ?
C21 C26 1.386(3) . ?
C21 B2 1.608(3) . ?
C22 C23 1.383(3) . ?
C23 C24 1.383(3) . ?
C24 C25 1.377(3) . ?
C25 C26 1.390(3) . ?
C27 C28 1.396(2) . ?
C27 C32 1.388(3) . ?
C27 B3 1.580(2) . ?
C28 C29 1.388(3) . ?
C29 C30 1.376(3) . ?
C30 C31 1.386(3) . ?
C31 C32 1.391(3) . ?
N3 C34 1.429(3) . ?
C34 C35A 1.497(5) . ?
C34 C35B 1.564(12) . ?
C35A C36A 1.373(7) . ?
C35A C40A 1.364(7) . ?
C36A C37A 1.381(4) . ?
C37A C38A 1.369(5) . ?
C38A C39A 1.369(5) . ?
C39A C40A 1.389(4) . ?
C35B C36B 1.424(12) . ?
C35B C40B 1.402(11) . ?
C36B C37B 1.387(11) . ?
C37B C38B 1.395(10) . ?
C38B C39B 1.376(10) . ?
C39B C40B 1.376(9) . ?
N4 C41 1.436(3) . ?
C41 C42 1.522(3) . ?
C42 C43 1.389(3) . ?
C42 C47 1.385(3) . ?
C43 C44 1.374(3) . ?
C44 C45 1.375(3) . ?
C45 C46 1.381(3) . ?
C46 C47 1.392(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
B2 O1 B1 122.04(13) . . ?
B3 O2 B2 118.99(14) . . ?
B3 O3 B1 120.85(13) . . ?
C1 N1 B1 115.44(13) . . ?
C14 N2 B2 115.83(13) . . ?
N1 C1 C2 112.23(15) . . ?
C4A C3A C2 120.2(8) . . ?
C5A C4A C3A 118.8(8) . . ?
C4A C5A C6A 121.8(6) . . ?
C5A C6A C7A 119.8(8) . . ?
C2 C7A C6A 118.1(10) . . ?
C4B C3B C2 122.0(8) . . ?
C3B C4B C5B 120.7(7) . . ?
C4B C5B C6B 120.3(6) . . ?
C5B C6B C7B 117.6(8) . . ?
C2 C7B C6B 122.0(9) . . ?
C9 C8 B1 121.68(15) . . ?
C13 C8 C9 115.57(17) . . ?
C13 C8 B1 122.71(15) . . ?
C10 C9 C8 122.50(18) . . ?
C11 C10 C9 120.07(19) . . ?
C12 C11 C10 119.0(2) . . ?
C11 C12 C13 120.31(19) . . ?
C12 C13 C8 122.50(17) . . ?
N2 C14 C15 113.05(14) . . ?
C16 C15 C14 120.78(17) . . ?
C16 C15 C20 118.49(17) . . ?
C20 C15 C14 120.72(17) . . ?
C17 C16 C15 120.59(18) . . ?
C18 C17 C16 120.2(2) . . ?
C19 C18 C17 119.66(19) . . ?
C18 C19 C20 120.57(19) . . ?
C19 C20 C15 120.51(19) . . ?
C22 C21 B2 120.45(16) . . ?
C26 C21 C22 116.05(16) . . ?
C26 C21 B2 123.43(15) . . ?
C23 C22 C21 122.6(2) . . ?
C24 C23 C22 119.83(19) . . ?
C25 C24 C23 119.12(18) . . ?
C24 C25 C26 120.06(19) . . ?
C21 C26 C25 122.31(17) . . ?
C28 C27 B3 120.68(17) . . ?
C32 C27 C28 117.21(16) . . ?
C32 C27 B3 122.05(15) . . ?
C29 C28 C27 121.38(19) . . ?
C30 C29 C28 120.05(18) . . ?
C29 C30 C31 120.10(18) . . ?
C30 C31 C32 119.2(2) . . ?
C27 C32 C31 122.06(18) . . ?
O1 B1 O3 114.77(15) . . ?
O1 B1 N1 104.31(13) . . ?
O1 B1 C8 113.23(15) . . ?
O3 B1 N1 103.16(14) . . ?
O3 B1 C8 112.55(14) . . ?
C8 B1 N1 107.66(14) . . ?
O1 B2 O2 115.10(14) . . ?
O1 B2 N2 105.96(15) . . ?
O1 B2 C21 111.62(14) . . ?
O2 B2 N2 101.78(12) . . ?
O2 B2 C21 112.34(15) . . ?
C21 B2 N2 109.21(13) . . ?
O2 B3 O3 122.66(16) . . ?
O2 B3 C27 119.50(17) . . ?
O3 B3 C27 117.80(15) . . ?
N3 C34 C35A 120.2(5) . . ?
N3 C34 C35B 113.5(10) . . ?
C36A C35A C34 120.0(5) . . ?
C40A C35A C34 121.7(5) . . ?
C40A C35A C36A 118.2(4) . . ?
C35A C36A C37A 121.0(4) . . ?
C38A C37A C36A 120.1(3) . . ?
C39A C38A C37A 119.6(3) . . ?
C38A C39A C40A 119.5(3) . . ?
C35A C40A C39A 121.4(4) . . ?
C36B C35B C34 117.8(9) . . ?
C40B C35B C34 126.2(9) . . ?
C40B C35B C36B 116.0(10) . . ?
C37B C36B C35B 122.3(10) . . ?
C36B C37B C38B 118.3(10) . . ?
C39B C38B C37B 121.1(10) . . ?
C38B C39B C40B 119.9(8) . . ?
C39B C40B C35B 122.3(8) . . ?
N4 C41 C42 118.89(17) . . ?
C43 C42 C41 117.82(17) . . ?
C47 C42 C41 124.16(17) . . ?
C47 C42 C43 118.01(17) . . ?
C44 C43 C42 121.60(18) . . ?
C43 C44 C45 120.06(18) . . ?
C44 C45 C46 119.57(18) . . ?
C45 C46 C47 120.22(17) . . ?
C42 C47 C46 120.55(17) . . ?
C3A C2 C1 112.5(4) . . ?
C7A C2 C1 126.1(6) . . ?
C7A C2 C3A 121.0(7) . . ?
C3B C2 C1 127.1(4) . . ?
C3B C2 C7B 117.1(7) . . ?
C7B C2 C1 115.6(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
N1 H1B N3 0.94(2) 2.00(2) 2.933(3) 172(2) .
N2 H2B N4 0.93(2) 2.12(2) 3.038(2) 168.9(17) .

####################################################################### 
# 
# 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_11c_16srv268
_database_code_depnum_ccdc_archive 'CCDC 1551623'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2016-07-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;

_chemical_name_common            ?
_chemical_name_systematic        
'Di-2-chlorophenylboronic B-O-B di-2-phenylacetate '
_chemical_formula_moiety         'C28 H22 B2 Cl2 O5'
_chemical_formula_sum            'C28 H22 B2 Cl2 O5'
_chemical_formula_weight         530.97
_chemical_melting_point          429(4)
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'
O O 0.0106 0.0060 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4296(5)
_cell_length_b                   11.1470(6)
_cell_length_c                   11.7996(6)
_cell_angle_alpha                84.748(2)
_cell_angle_beta                 87.958(2)
_cell_angle_gamma                67.5356(19)
_cell_volume                     1262.39(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9604
_cell_measurement_temperature    120
_cell_measurement_theta_max      33.17
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1166 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.9520.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             548
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -1.00 0.1360
0.00 -1.00 1.00 0.2100
1.00 0.00 0.00 0.1020
-1.00 0.00 0.00 0.1070
-1.00 1.00 0.00 0.1330
1.00 -1.00 0.00 0.1380
1.00 0.00 -1.00 0.1270
0.00 0.00 1.00 0.2850
1.00 -1.00 2.00 0.2000
0.00 0.00 -1.00 0.1440
1.00 -1.00 -2.00 0.1540
-1.00 -2.00 0.00 0.2500
1.00 2.00 0.00 0.1890
2.00 1.00 1.00 0.1970
-2.00 -2.00 -1.00 0.2160

_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.214
_exptl_special_details           
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of narrow-frame ω-scans (3 run 
of 340 and one of 181 scans, scan width 0.5°, 5s exposure), every run 
at a different φ angle. Two runs of 358 φ-scans (scan width 1°, 1s 
exposure) were used for scaling overflowing intensities. 
Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28237
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        33.199
_diffrn_reflns_theta_max         33.199
_diffrn_reflns_theta_min         2.522
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7311
_reflns_number_total             9620
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         9620
_refine_ls_number_restraints     309
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.019
_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)+(0.0510P)²+0.3420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1111
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.23660(3) 0.75897(3) 0.36266(3) 0.03314(8) Uani 1 1 d . U . . .
Cl2 Cl 0.85882(3) 0.18869(3) 0.32567(3) 0.02981(8) Uani 1 1 d . U . . .
O1 O 0.48929(7) 0.55912(7) 0.20218(6) 0.01613(14) Uani 1 1 d . U . . .
O2 O 0.33553(8) 0.46927(8) 0.30597(7) 0.02162(16) Uani 1 1 d . U . . .
O3 O 0.55829(8) 0.39482(8) 0.36060(7) 0.01941(15) Uani 1 1 d . U . . .
O4 O 0.38331(8) 0.43720(8) 0.10740(7) 0.02072(16) Uani 1 1 d . U . . .
O5 O 0.60273(8) 0.33096(7) 0.16740(7) 0.01899(15) Uani 1 1 d . U . . .
C1 C 0.22748(11) 0.66426(11) 0.15811(9) 0.0195(2) Uani 1 1 d . U . . .
C2 C 0.16614(12) 0.76530(12) 0.22840(11) 0.0247(2) Uani 1 1 d . U . . .
C3 C 0.04741(14) 0.87428(13) 0.19783(13) 0.0342(3) Uani 1 1 d . U . . .
H3 H 0.0084 0.9407 0.2483 0.041 Uiso 1 1 calc R . . . .
C4 C -0.01292(14) 0.88451(14) 0.09299(13) 0.0371(3) Uani 1 1 d . U . . .
H4 H -0.0940 0.9582 0.0712 0.045 Uiso 1 1 calc R . . . .
C5 C 0.04479(13) 0.78756(14) 0.01994(12) 0.0319(3) Uani 1 1 d . U . . .
H5 H 0.0043 0.7950 -0.0525 0.038 Uiso 1 1 calc R . . . .
C6 C 0.16258(12) 0.67903(12) 0.05304(10) 0.0235(2) Uani 1 1 d . U . . .
H6 H 0.2003 0.6125 0.0024 0.028 Uiso 1 1 calc R . . . .
C7 C 0.74938(11) 0.44375(11) 0.24135(9) 0.01771(19) Uani 1 1 d . U . . .
C8 C 0.87023(12) 0.33586(11) 0.27109(10) 0.0213(2) Uani 1 1 d . U . . .
C9 C 1.00247(12) 0.33825(14) 0.25907(11) 0.0284(3) Uani 1 1 d . U . . .
H9 H 1.0821 0.2628 0.2804 0.034 Uiso 1 1 calc R . . . .
C10 C 1.01604(13) 0.45232(15) 0.21546(12) 0.0322(3) Uani 1 1 d . U . . .
H10 H 1.1057 0.4550 0.2052 0.039 Uiso 1 1 calc R . . . .
C11 C 0.89935(13) 0.56266(14) 0.18675(11) 0.0289(3) Uani 1 1 d . U . . .
H11 H 0.9087 0.6413 0.1579 0.035 Uiso 1 1 calc R . . . .
C12 C 0.76834(12) 0.55776(12) 0.20030(10) 0.0218(2) Uani 1 1 d . U . . .
H12 H 0.6891 0.6343 0.1811 0.026 Uiso 1 1 calc R . . . .
C13 C 0.43057(11) 0.41610(11) 0.37988(9) 0.0195(2) Uani 1 1 d . U . . .
C14 C 0.39092(13) 0.37780(13) 0.49649(10) 0.0260(2) Uani 1 1 d . U . . .
H14A H 0.3389 0.4577 0.5349 0.031 Uiso 1 1 calc R . . . .
H14B H 0.4764 0.3280 0.5409 0.031 Uiso 1 1 calc R . . . .
C15 C 0.30339(11) 0.29643(11) 0.49699(9) 0.0195(2) Uani 1 1 d . U . . .
C16 C 0.16917(12) 0.34452(14) 0.53979(10) 0.0265(2) Uani 1 1 d . U . . .
H16 H 0.1307 0.4305 0.5631 0.032 Uiso 1 1 calc R . . . .
C17 C 0.09131(15) 0.26766(18) 0.54859(12) 0.0398(3) Uani 1 1 d . U . . .
H17 H -0.0001 0.3008 0.5786 0.048 Uiso 1 1 calc R . . . .
C18 C 0.14560(19) 0.14362(18) 0.51408(13) 0.0452(4) Uani 1 1 d . U . . .
H18 H 0.0924 0.0906 0.5216 0.054 Uiso 1 1 calc R . . . .
C19 C 0.2774(2) 0.09597(15) 0.46853(12) 0.0416(4) Uani 1 1 d . U . . .
H19 H 0.3139 0.0110 0.4430 0.050 Uiso 1 1 calc R . . . .
C20 C 0.35728(15) 0.17219(13) 0.45987(11) 0.0297(3) Uani 1 1 d . U . . .
H20 H 0.4482 0.1392 0.4287 0.036 Uiso 1 1 calc R . . . .
C21 C 0.50086(12) 0.34295(10) 0.10548(9) 0.01874(19) Uani 1 1 d . U . . .
C22 C 0.51861(14) 0.23640(11) 0.03089(10) 0.0232(2) Uani 1 1 d . U . . .
H22A H 0.6128 0.2058 -0.0027 0.028 Uiso 1 1 calc R . . . .
H22B H 0.4502 0.2692 -0.0319 0.028 Uiso 1 1 calc R . . . .
C23 C 0.49745(11) 0.12506(10) 0.10170(9) 0.01796(19) Uani 1 1 d . U . . .
C24 C 0.37226(13) 0.10818(12) 0.09790(11) 0.0264(2) Uani 1 1 d . U . . .
H24 H 0.2979 0.1686 0.0528 0.032 Uiso 1 1 calc R . . . .
C25 C 0.35627(16) 0.00285(15) 0.16011(13) 0.0368(3) Uani 1 1 d . U . . .
H25 H 0.2707 -0.0086 0.1576 0.044 Uiso 1 1 calc R . . . .
C26 C 0.46422(18) -0.08551(14) 0.22572(12) 0.0380(3) Uani 1 1 d . U . . .
H26 H 0.4535 -0.1586 0.2665 0.046 Uiso 1 1 calc R . . . .
C27 C 0.58745(16) -0.06772(13) 0.23211(11) 0.0324(3) Uani 1 1 d . U . . .
H27 H 0.6610 -0.1277 0.2782 0.039 Uiso 1 1 calc R . . . .
C28 C 0.60373(12) 0.03794(11) 0.17107(10) 0.0233(2) Uani 1 1 d . U . . .
H28 H 0.6881 0.0510 0.1766 0.028 Uiso 1 1 calc R . . . .
B1 B 0.36421(12) 0.54045(12) 0.19261(10) 0.0178(2) Uani 1 1 d . U . . .
B2 B 0.59761(12) 0.44246(11) 0.24124(10) 0.0167(2) Uani 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
Cl1 C2 1.7543(13) . ?
Cl2 C8 1.7523(12) . ?
O1 B1 1.4072(13) . ?
O1 B2 1.4087(14) . ?
O2 C13 1.2698(14) . ?
O2 B1 1.5705(14) . ?
O3 C13 1.2764(13) . ?
O3 B2 1.5563(14) . ?
O4 C21 1.2749(14) . ?
O4 B1 1.5485(14) . ?
O5 C21 1.2687(13) . ?
O5 B2 1.5655(14) . ?
C1 C2 1.3958(16) . ?
C1 C6 1.3998(17) . ?
C1 B1 1.5933(17) . ?
C2 C3 1.3933(19) . ?
C3 C4 1.383(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.3919(17) . ?
C7 C8 1.3979(16) . ?
C7 C12 1.4005(15) . ?
C7 B2 1.5886(16) . ?
C8 C9 1.3916(16) . ?
C9 C10 1.3835(19) . ?
C10 C11 1.385(2) . ?
C11 C12 1.3912(16) . ?
C13 C14 1.4945(15) . ?
C14 C15 1.5125(15) . ?
C15 C16 1.3884(16) . ?
C15 C20 1.3872(18) . ?
C16 C17 1.3834(19) . ?
C17 C18 1.373(3) . ?
C18 C19 1.379(3) . ?
C19 C20 1.395(2) . ?
C21 C22 1.4938(15) . ?
C22 C23 1.5143(15) . ?
C23 C24 1.3913(16) . ?
C23 C28 1.3922(16) . ?
C24 C25 1.3887(19) . ?
C25 C26 1.383(2) . ?
C26 C27 1.379(2) . ?
C27 C28 1.3869(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
B1 O1 B2 111.23(8) . . ?
C13 O2 B1 120.41(8) . . ?
C13 O3 B2 117.69(9) . . ?
C21 O4 B1 117.51(9) . . ?
C21 O5 B2 121.07(9) . . ?
C2 C1 C6 115.74(11) . . ?
C2 C1 B1 122.90(11) . . ?
C6 C1 B1 121.36(10) . . ?
C1 C2 Cl1 120.46(10) . . ?
C3 C2 Cl1 116.57(10) . . ?
C3 C2 C1 122.96(12) . . ?
C4 C3 C2 119.16(12) . . ?
C5 C4 C3 120.02(12) . . ?
C4 C5 C6 119.67(13) . . ?
C5 C6 C1 122.44(12) . . ?
C8 C7 C12 115.83(10) . . ?
C8 C7 B2 125.13(10) . . ?
C12 C7 B2 118.83(10) . . ?
C7 C8 Cl2 119.80(8) . . ?
C9 C8 Cl2 117.08(9) . . ?
C9 C8 C7 123.12(11) . . ?
C10 C9 C8 118.88(12) . . ?
C9 C10 C11 120.22(11) . . ?
C10 C11 C12 119.68(12) . . ?
C11 C12 C7 122.23(11) . . ?
O2 C13 O3 123.64(10) . . ?
O2 C13 C14 118.39(10) . . ?
O3 C13 C14 117.97(10) . . ?
C13 C14 C15 113.62(9) . . ?
C16 C15 C14 119.51(11) . . ?
C20 C15 C14 120.94(11) . . ?
C20 C15 C16 119.48(11) . . ?
C17 C16 C15 120.25(13) . . ?
C18 C17 C16 120.31(14) . . ?
C17 C18 C19 120.01(13) . . ?
C18 C19 C20 120.22(14) . . ?
C15 C20 C19 119.69(13) . . ?
O4 C21 C22 118.63(10) . . ?
O5 C21 O4 123.74(10) . . ?
O5 C21 C22 117.55(10) . . ?
C21 C22 C23 108.87(9) . . ?
C24 C23 C22 120.56(11) . . ?
C24 C23 C28 119.25(11) . . ?
C28 C23 C22 120.19(10) . . ?
C25 C24 C23 119.86(12) . . ?
C26 C25 C24 120.34(12) . . ?
C27 C26 C25 120.14(12) . . ?
C26 C27 C28 119.83(13) . . ?
C27 C28 C23 120.52(12) . . ?
O1 B1 O2 109.71(9) . . ?
O1 B1 O4 109.52(9) . . ?
O1 B1 C1 118.29(9) . . ?
O2 B1 C1 108.73(8) . . ?
O4 B1 O2 101.09(8) . . ?
O4 B1 C1 108.11(9) . . ?
O1 B2 O3 108.92(8) . . ?
O1 B2 O5 109.31(9) . . ?
O1 B2 C7 117.01(9) . . ?
O3 B2 O5 102.02(8) . . ?
O3 B2 C7 111.28(9) . . ?
O5 B2 C7 107.22(8) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'


####################################################################### 
# 
# 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_10c_15srv282
_database_code_depnum_ccdc_archive 'CCDC 1551621'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_date             2015-11-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_chemical_name_common            ?
_chemical_name_systematic        
; phenylboroxine complex with 2 equiv. benzylamine
;
_chemical_formula_moiety         'C25 H24 B3 N O3, C7 H9 N'
_chemical_formula_sum            'C32 H33 B3 N2 O3'
_chemical_formula_weight         526.03
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.2396(4)
_cell_length_b                   15.2054(6)
_cell_length_c                   17.9361(7)
_cell_angle_alpha                89.7333(16)
_cell_angle_beta                 72.0196(15)
_cell_angle_gamma                84.3291(17)
_cell_volume                     2900.27(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9200
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1546 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.8866.
The λ/2 correction factor is Not present.
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 -1.00 0.1000
1.00 0.00 1.00 0.0810
0.00 0.00 1.00 0.1350
0.00 0.00 -1.00 0.1710
-1.00 0.00 2.00 0.1630
0.00 -1.00 -1.00 0.3190
0.00 1.00 1.00 0.2900
-1.00 -2.00 1.00 0.2320
1.00 2.00 -1.00 0.2180
1.00 2.00 0.00 0.2370
2.00 0.00 -1.00 0.1660
0.00 -1.00 0.00 0.3370
0.00 -1.00 1.00 0.2130
0.00 2.00 -1.00 0.2530

_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: benzylamine, toluene'
_exptl_crystal_size_max          0.683
_exptl_crystal_size_mid          0.379
_exptl_crystal_size_min          0.2
_exptl_special_details           
; Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of narrow-frame ω-scans (scan 
width 0.5°, 5s exposure), every run at a different φ angle.
Two runs of φ-scans (scan width 1°, 1s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            55370
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         2.247
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10461
_reflns_number_total             13416
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     753
_refine_ls_number_reflns         13416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.030
_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)+(0.0430P)²+0.9460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1087
_refine_special_details          
; Amino H atoms - refall, other H - riding (constr).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C33(H33A,H33B), C26(H26A,H26B), C58(H58A,H58B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
  C23(H23), C24(H24), C25(H25), C35(H35), C36(H36), C37(H37), C38(H38),
 C39(H39), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48),
  C49(H49), C50(H50), C51(H51), C53(H53), C54(H54), C55(H55), C56(H56),
 C57(H57), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C60(H60), C61(H61),
  C62(H62), C63(H63), C64(H64)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44951(8) 0.11540(6) 0.76979(5) 0.02017(19) Uani 1 1 d . . . . .
O2 O 0.30947(8) 0.09005(6) 0.69721(5) 0.0229(2) Uani 1 1 d . . . . .
O3 O 0.23983(8) 0.19492(6) 0.80409(5) 0.02035(19) Uani 1 1 d . . . . .
N1 N 0.30586(10) 0.11138(7) 0.90239(7) 0.0192(2) Uani 1 1 d . . . . .
H1A H 0.2796(14) 0.0625(11) 0.8823(9) 0.027(4) Uiso 1 1 d . . . . .
H1B H 0.2359(15) 0.1399(10) 0.9375(9) 0.025(4) Uiso 1 1 d . . . . .
C1 C 0.39910(12) 0.08048(9) 0.94306(8) 0.0250(3) Uani 1 1 d . . . . .
H1C H 0.4194 0.1314 0.9694 0.030 Uiso 1 1 calc R . . . .
H1D H 0.4776 0.0540 0.9042 0.030 Uiso 1 1 calc R . . . .
C2 C 0.34665(11) 0.01303(9) 1.00274(8) 0.0210(3) Uani 1 1 d . . . . .
C3 C 0.36033(13) -0.07599(9) 0.98160(8) 0.0271(3) Uani 1 1 d . . . . .
H3 H 0.4100 -0.0955 0.9302 0.032 Uiso 1 1 calc R . . . .
C4 C 0.30211(14) -0.13669(10) 1.03503(10) 0.0333(3) Uani 1 1 d . . . . .
H4 H 0.3111 -0.1974 1.0199 0.040 Uiso 1 1 calc R . . . .
C5 C 0.23107(14) -0.10918(10) 1.11022(9) 0.0344(4) Uani 1 1 d . . . . .
H5 H 0.1900 -0.1506 1.1465 0.041 Uiso 1 1 calc R . . . .
C6 C 0.21993(14) -0.02141(11) 1.13245(9) 0.0343(3) Uani 1 1 d . . . . .
H6 H 0.1729 -0.0025 1.1845 0.041 Uiso 1 1 calc R . . . .
C7 C 0.27730(13) 0.03943(9) 1.07889(8) 0.0274(3) Uani 1 1 d . . . . .
H7 H 0.2690 0.0999 1.0946 0.033 Uiso 1 1 calc R . . . .
C8 C 0.40521(11) 0.26053(8) 0.84958(7) 0.0181(2) Uani 1 1 d . . . . .
C9 C 0.53055(12) 0.26300(9) 0.84584(8) 0.0219(3) Uani 1 1 d . . . . .
H9 H 0.5871 0.2108 0.8306 0.026 Uiso 1 1 calc R . . . .
C10 C 0.57509(12) 0.33940(9) 0.86374(8) 0.0261(3) Uani 1 1 d . . . . .
H10 H 0.6608 0.3388 0.8613 0.031 Uiso 1 1 calc R . . . .
C11 C 0.49498(13) 0.41648(9) 0.88515(8) 0.0269(3) Uani 1 1 d . . . . .
H11 H 0.5254 0.4690 0.8971 0.032 Uiso 1 1 calc R . . . .
C12 C 0.36986(13) 0.41630(9) 0.88906(9) 0.0276(3) Uani 1 1 d . . . . .
H12 H 0.3142 0.4690 0.9034 0.033 Uiso 1 1 calc R . . . .
C13 C 0.32622(12) 0.33917(9) 0.87200(8) 0.0230(3) Uani 1 1 d . . . . .
H13 H 0.2400 0.3397 0.8757 0.028 Uiso 1 1 calc R . . . .
C14 C 0.52891(12) 0.00474(8) 0.65767(8) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.64195(13) -0.01582(10) 0.67421(9) 0.0296(3) Uani 1 1 d . . . . .
H15 H 0.6549 0.0125 0.7178 0.035 Uiso 1 1 calc R . . . .
C16 C 0.73565(14) -0.07677(10) 0.62823(9) 0.0358(4) Uani 1 1 d . . . . .
H16 H 0.8119 -0.0899 0.6404 0.043 Uiso 1 1 calc R . . . .
C17 C 0.71780(14) -0.11835(10) 0.56465(10) 0.0356(4) Uani 1 1 d . . . . .
H17 H 0.7818 -0.1602 0.5332 0.043 Uiso 1 1 calc R . . . .
C18 C 0.60731(15) -0.09916(10) 0.54684(10) 0.0355(3) Uani 1 1 d . . . . .
H18 H 0.5952 -0.1276 0.5031 0.043 Uiso 1 1 calc R . . . .
C19 C 0.51390(13) -0.03814(9) 0.59312(9) 0.0284(3) Uani 1 1 d . . . . .
H19 H 0.4380 -0.0253 0.5805 0.034 Uiso 1 1 calc R . . . .
C20 C 0.09126(12) 0.17675(9) 0.72747(7) 0.0214(3) Uani 1 1 d . . . . .
C21 C 0.04325(14) 0.11956(11) 0.68632(8) 0.0326(3) Uani 1 1 d . . . . .
H21 H 0.0902 0.0648 0.6661 0.039 Uiso 1 1 calc R . . . .
C22 C -0.07281(15) 0.14151(13) 0.67439(9) 0.0419(4) Uani 1 1 d . . . . .
H22 H -0.1054 0.1010 0.6476 0.050 Uiso 1 1 calc R . . . .
C23 C -0.14025(14) 0.22188(13) 0.70143(9) 0.0409(4) Uani 1 1 d . . . . .
H23 H -0.2180 0.2377 0.6917 0.049 Uiso 1 1 calc R . . . .
C24 C -0.09473(13) 0.27910(11) 0.74246(9) 0.0345(4) Uani 1 1 d . . . . .
H24 H -0.1414 0.3344 0.7614 0.041 Uiso 1 1 calc R . . . .
C25 C 0.01897(12) 0.25653(9) 0.75641(8) 0.0255(3) Uani 1 1 d . . . . .
H25 H 0.0482 0.2960 0.7862 0.031 Uiso 1 1 calc R . . . .
B1 B 0.35354(13) 0.17359(9) 0.82660(8) 0.0182(3) Uani 1 1 d . . . . .
B2 B 0.42500(13) 0.07360(10) 0.71107(9) 0.0205(3) Uani 1 1 d . . . . .
B3 B 0.22030(13) 0.15324(9) 0.74368(8) 0.0198(3) Uani 1 1 d . . . . .
O4 O 0.13359(8) 0.63390(6) 0.69643(5) 0.01979(19) Uani 1 1 d . . . . .
O5 O 0.27133(8) 0.73073(6) 0.72213(5) 0.0233(2) Uani 1 1 d . . . . .
O6 O 0.23949(8) 0.59923(6) 0.79503(5) 0.01988(19) Uani 1 1 d . . . . .
N3 N 0.23366(10) 0.48315(7) 0.70021(7) 0.0195(2) Uani 1 1 d . . . . .
H3A H 0.2431(14) 0.4389(11) 0.7330(9) 0.029(4) Uiso 1 1 d . . . . .
H3B H 0.1839(17) 0.4625(11) 0.6721(10) 0.042(5) Uiso 1 1 d . . . . .
C33 C 0.35936(12) 0.49463(9) 0.64291(8) 0.0250(3) Uani 1 1 d . . . . .
H33A H 0.4100 0.5242 0.6697 0.030 Uiso 1 1 calc R . . . .
H33B H 0.3480 0.5331 0.6004 0.030 Uiso 1 1 calc R . . . .
C34 C 0.42879(11) 0.40726(8) 0.60801(8) 0.0208(3) Uani 1 1 d . . . . .
C35 C 0.45377(12) 0.38617(9) 0.52910(8) 0.0247(3) Uani 1 1 d . . . . .
H35 H 0.4258 0.4269 0.4962 0.030 Uiso 1 1 calc R . . . .
C36 C 0.51954(14) 0.30564(10) 0.49802(9) 0.0317(3) Uani 1 1 d . . . . .
H36 H 0.5368 0.2916 0.4439 0.038 Uiso 1 1 calc R . . . .
C37 C 0.55994(13) 0.24591(9) 0.54573(9) 0.0312(3) Uani 1 1 d . . . . .
H37 H 0.6053 0.1910 0.5243 0.037 Uiso 1 1 calc R . . . .
C38 C 0.53428(12) 0.26615(9) 0.62443(9) 0.0281(3) Uani 1 1 d . . . . .
H38 H 0.5610 0.2248 0.6573 0.034 Uiso 1 1 calc R . . . .
C39 C 0.46986(12) 0.34639(9) 0.65534(8) 0.0247(3) Uani 1 1 d . . . . .
H39 H 0.4534 0.3603 0.7094 0.030 Uiso 1 1 calc R . . . .
C40 C 0.02980(11) 0.53579(8) 0.80993(7) 0.0178(2) Uani 1 1 d . . . . .
C41 C 0.02809(12) 0.49216(8) 0.87895(7) 0.0212(3) Uani 1 1 d . . . . .
H41 H 0.1035 0.4832 0.8926 0.025 Uiso 1 1 calc R . . . .
C42 C -0.08052(13) 0.46146(9) 0.92819(8) 0.0248(3) Uani 1 1 d . . . . .
H42 H -0.0787 0.4318 0.9746 0.030 Uiso 1 1 calc R . . . .
C43 C -0.19135(13) 0.47413(9) 0.90940(8) 0.0260(3) Uani 1 1 d . . . . .
H43 H -0.2661 0.4537 0.9430 0.031 Uiso 1 1 calc R . . . .
C44 C -0.19254(12) 0.51694(9) 0.84119(8) 0.0254(3) Uani 1 1 d . . . . .
H44 H -0.2684 0.5259 0.8280 0.031 Uiso 1 1 calc R . . . .
C45 C -0.08313(12) 0.54676(8) 0.79202(7) 0.0204(3) Uani 1 1 d . . . . .
H45 H -0.0852 0.5753 0.7451 0.025 Uiso 1 1 calc R . . . .
C46 C 0.15601(11) 0.78005(8) 0.62658(7) 0.0197(3) Uani 1 1 d . . . . .
C47 C 0.08284(12) 0.76208(9) 0.57922(8) 0.0238(3) Uani 1 1 d . . . . .
H47 H 0.0460 0.7079 0.5843 0.029 Uiso 1 1 calc R . . . .
C48 C 0.06312(13) 0.82225(10) 0.52483(8) 0.0286(3) Uani 1 1 d . . . . .
H48 H 0.0140 0.8087 0.4926 0.034 Uiso 1 1 calc R . . . .
C49 C 0.11480(13) 0.90207(9) 0.51741(8) 0.0278(3) Uani 1 1 d . . . . .
H49 H 0.1009 0.9433 0.4803 0.033 Uiso 1 1 calc R . . . .
C50 C 0.18659(13) 0.92165(9) 0.56409(8) 0.0253(3) Uani 1 1 d . . . . .
H50 H 0.2219 0.9765 0.5593 0.030 Uiso 1 1 calc R . . . .
C51 C 0.20707(12) 0.86104(9) 0.61803(8) 0.0232(3) Uani 1 1 d . . . . .
H51 H 0.2568 0.8749 0.6498 0.028 Uiso 1 1 calc R . . . .
C52 C 0.39831(12) 0.69850(8) 0.81482(8) 0.0210(3) Uani 1 1 d . . . . .
C53 C 0.48290(13) 0.75930(9) 0.77943(8) 0.0258(3) Uani 1 1 d . . . . .
H53 H 0.4741 0.7894 0.7346 0.031 Uiso 1 1 calc R . . . .
C54 C 0.57934(14) 0.77645(10) 0.80865(9) 0.0324(3) Uani 1 1 d . . . . .
H54 H 0.6366 0.8174 0.7835 0.039 Uiso 1 1 calc R . . . .
C55 C 0.59192(14) 0.73390(10) 0.87443(10) 0.0337(3) Uani 1 1 d . . . . .
H55 H 0.6582 0.7453 0.8943 0.040 Uiso 1 1 calc R . . . .
C56 C 0.50821(15) 0.67475(10) 0.91140(9) 0.0332(3) Uani 1 1 d . . . . .
H56 H 0.5162 0.6461 0.9571 0.040 Uiso 1 1 calc R . . . .
C57 C 0.41271(13) 0.65739(9) 0.88171(8) 0.0271(3) Uani 1 1 d . . . . .
H57 H 0.3557 0.6166 0.9074 0.033 Uiso 1 1 calc R . . . .
B4 B 0.15670(13) 0.56986(9) 0.75276(8) 0.0183(3) Uani 1 1 d . . . . .
B5 B 0.18607(13) 0.71047(10) 0.68466(8) 0.0195(3) Uani 1 1 d . . . . .
B6 B 0.29609(13) 0.67404(10) 0.77716(8) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.22821(12) -0.04798(9) 0.83916(8) 0.0312(3) Uani 1 1 d . . . . .
H2A H 0.2206(19) -0.0487(14) 0.7914(13) 0.058(6) Uiso 1 1 d . . . . .
H2B H 0.2744(19) -0.1031(14) 0.8449(12) 0.058(6) Uiso 1 1 d . . . . .
C26 C 0.10327(13) -0.04380(10) 0.89817(10) 0.0326(3) Uani 1 1 d . . . . .
H26A H 0.0476 0.0032 0.8837 0.039 Uiso 1 1 calc R . . . .
H26B H 0.1113 -0.0261 0.9493 0.039 Uiso 1 1 calc R . . . .
C27 C 0.04014(12) -0.12830(9) 0.90855(9) 0.0275(3) Uani 1 1 d . . . . .
C28 C 0.01575(13) -0.17149(10) 0.97905(9) 0.0315(3) Uani 1 1 d . . . . .
H28 H 0.0411 -0.1486 1.0203 0.038 Uiso 1 1 calc R . . . .
C29 C -0.04533(14) -0.24785(10) 0.99016(10) 0.0364(4) Uani 1 1 d . . . . .
H29 H -0.0616 -0.2768 1.0388 0.044 Uiso 1 1 calc R . . . .
C30 C -0.08246(14) -0.28174(10) 0.93055(10) 0.0377(4) Uani 1 1 d . . . . .
H30 H -0.1255 -0.3334 0.9384 0.045 Uiso 1 1 calc R . . . .
C31 C -0.05660(13) -0.24017(10) 0.85945(10) 0.0341(3) Uani 1 1 d . . . . .
H31 H -0.0807 -0.2639 0.8180 0.041 Uiso 1 1 calc R . . . .
C32 C 0.00438(13) -0.16404(9) 0.84846(9) 0.0302(3) Uani 1 1 d . . . . .
H32 H 0.0220 -0.1360 0.7994 0.036 Uiso 1 1 calc R . . . .
N4 N 0.06124(13) 0.42735(10) 0.61848(7) 0.0316(3) Uani 1 1 d . . . . .
H4A H 0.0202(18) 0.3920(13) 0.6556(12) 0.051(5) Uiso 1 1 d . . . . .
H4B H 0.0007(19) 0.4723(13) 0.6133(11) 0.052(6) Uiso 1 1 d . . . . .
C58 C 0.10996(15) 0.37504(10) 0.54524(9) 0.0326(3) Uani 1 1 d . . . . .
H58A H 0.0397 0.3485 0.5346 0.039 Uiso 1 1 calc R . . . .
H58B H 0.1709 0.3262 0.5515 0.039 Uiso 1 1 calc R . . . .
C59 C 0.17360(13) 0.42860(9) 0.47589(8) 0.0248(3) Uani 1 1 d . . . . .
C60 C 0.22700(15) 0.38679(10) 0.40270(9) 0.0335(3) Uani 1 1 d . . . . .
H60 H 0.2218 0.3253 0.3971 0.040 Uiso 1 1 calc R . . . .
C61 C 0.28751(15) 0.43329(12) 0.33800(9) 0.0370(4) Uani 1 1 d . . . . .
H61 H 0.3242 0.4036 0.2885 0.044 Uiso 1 1 calc R . . . .
C62 C 0.29484(14) 0.52295(11) 0.34502(9) 0.0354(4) Uani 1 1 d . . . . .
H62 H 0.3357 0.5551 0.3005 0.042 Uiso 1 1 calc R . . . .
C63 C 0.24224(14) 0.56529(10) 0.41737(9) 0.0321(3) Uani 1 1 d . . . . .
H63 H 0.2473 0.6268 0.4226 0.039 Uiso 1 1 calc R . . . .
C64 C 0.18201(13) 0.51854(9) 0.48249(8) 0.0261(3) Uani 1 1 d . . . . .
H64 H 0.1463 0.5483 0.5320 0.031 Uiso 1 1 calc R . . . .


_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 B1 1.4580(16) . ?
O1 B2 1.3449(17) . ?
O2 B2 1.3947(17) . ?
O2 B3 1.3871(17) . ?
O3 B1 1.4619(16) . ?
O3 B3 1.3433(17) . ?
N1 C1 1.4908(16) . ?
N1 B1 1.6335(17) . ?
C1 C2 1.5049(18) . ?
C2 C3 1.3883(19) . ?
C2 C7 1.3857(19) . ?
C3 C4 1.386(2) . ?
C4 C5 1.380(2) . ?
C5 C6 1.377(2) . ?
C6 C7 1.386(2) . ?
C8 C9 1.3938(17) . ?
C8 C13 1.3979(18) . ?
C8 B1 1.5997(19) . ?
C9 C10 1.3860(19) . ?
C10 C11 1.383(2) . ?
C11 C12 1.3865(19) . ?
C12 C13 1.3854(19) . ?
C14 C15 1.3976(19) . ?
C14 C19 1.394(2) . ?
C14 B2 1.5668(19) . ?
C15 C16 1.388(2) . ?
C16 C17 1.383(2) . ?
C17 C18 1.379(2) . ?
C18 C19 1.389(2) . ?
C20 C21 1.392(2) . ?
C20 C25 1.3971(19) . ?
C20 B3 1.5725(18) . ?
C21 C22 1.394(2) . ?
C22 C23 1.378(3) . ?
C23 C24 1.374(2) . ?
C24 C25 1.3869(19) . ?
O4 B4 1.4627(16) . ?
O4 B5 1.3433(17) . ?
O5 B5 1.3867(17) . ?
O5 B6 1.3817(17) . ?
O6 B4 1.4700(16) . ?
O6 B6 1.3472(17) . ?
N3 C33 1.4944(16) . ?
N3 B4 1.6303(17) . ?
C33 C34 1.5055(18) . ?
C34 C35 1.3878(19) . ?
C34 C39 1.3930(19) . ?
C35 C36 1.389(2) . ?
C36 C37 1.384(2) . ?
C37 C38 1.380(2) . ?
C38 C39 1.3800(19) . ?
C40 C41 1.3975(17) . ?
C40 C45 1.3970(17) . ?
C40 B4 1.6102(18) . ?
C41 C42 1.3897(18) . ?
C42 C43 1.3832(19) . ?
C43 C44 1.3863(19) . ?
C44 C45 1.3901(18) . ?
C46 C47 1.3965(18) . ?
C46 C51 1.3975(18) . ?
C46 B5 1.5669(19) . ?
C47 C48 1.3868(19) . ?
C48 C49 1.385(2) . ?
C49 C50 1.381(2) . ?
C50 C51 1.3876(19) . ?
C52 C53 1.3990(18) . ?
C52 C57 1.3961(19) . ?
C52 B6 1.5750(19) . ?
C53 C54 1.388(2) . ?
C54 C55 1.381(2) . ?
C55 C56 1.382(2) . ?
C56 C57 1.384(2) . ?
N2 C26 1.4702(19) . ?
C26 C27 1.5117(19) . ?
C27 C28 1.385(2) . ?
C27 C32 1.391(2) . ?
C28 C29 1.389(2) . ?
C29 C30 1.380(2) . ?
C30 C31 1.382(2) . ?
C31 C32 1.386(2) . ?
N4 C58 1.462(2) . ?
C58 C59 1.509(2) . ?
C59 C60 1.391(2) . ?
C59 C64 1.3883(19) . ?
C60 C61 1.382(2) . ?
C61 C62 1.383(2) . ?
C62 C63 1.381(2) . ?
C63 C64 1.388(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B2 O1 B1 121.96(10) . . ?
B3 O2 B2 118.70(11) . . ?
B3 O3 B1 121.97(10) . . ?
C1 N1 B1 117.23(10) . . ?
N1 C1 C2 110.17(10) . . ?
C3 C2 C1 120.80(12) . . ?
C7 C2 C1 120.39(12) . . ?
C7 C2 C3 118.70(12) . . ?
C4 C3 C2 120.49(14) . . ?
C5 C4 C3 120.17(14) . . ?
C6 C5 C4 119.78(14) . . ?
C5 C6 C7 120.07(14) . . ?
C2 C7 C6 120.75(14) . . ?
C9 C8 C13 116.74(12) . . ?
C9 C8 B1 122.35(11) . . ?
C13 C8 B1 120.87(11) . . ?
C10 C9 C8 121.87(12) . . ?
C11 C10 C9 120.14(12) . . ?
C10 C11 C12 119.40(13) . . ?
C13 C12 C11 119.86(13) . . ?
C12 C13 C8 121.99(12) . . ?
C15 C14 B2 119.88(12) . . ?
C19 C14 C15 117.49(13) . . ?
C19 C14 B2 122.63(12) . . ?
C16 C15 C14 121.29(14) . . ?
C17 C16 C15 119.84(14) . . ?
C18 C17 C16 120.12(14) . . ?
C17 C18 C19 119.75(14) . . ?
C18 C19 C14 121.52(14) . . ?
C21 C20 C25 117.64(12) . . ?
C21 C20 B3 122.35(12) . . ?
C25 C20 B3 120.00(12) . . ?
C20 C21 C22 120.96(15) . . ?
C23 C22 C21 120.14(15) . . ?
C24 C23 C22 119.76(14) . . ?
C23 C24 C25 120.32(15) . . ?
C24 C25 C20 121.12(14) . . ?
O1 B1 O3 113.21(10) . . ?
O1 B1 N1 103.61(10) . . ?
O1 B1 C8 113.40(10) . . ?
O3 B1 N1 102.93(9) . . ?
O3 B1 C8 111.70(10) . . ?
C8 B1 N1 111.17(10) . . ?
O1 B2 O2 121.43(12) . . ?
O1 B2 C14 118.87(12) . . ?
O2 B2 C14 119.70(12) . . ?
O2 B3 C20 120.24(12) . . ?
O3 B3 O2 121.69(12) . . ?
O3 B3 C20 118.06(12) . . ?
B5 O4 B4 122.20(10) . . ?
B6 O5 B5 119.37(11) . . ?
B6 O6 B4 122.01(10) . . ?
C33 N3 B4 117.14(10) . . ?
N3 C33 C34 111.57(10) . . ?
C35 C34 C33 121.25(12) . . ?
C35 C34 C39 119.05(12) . . ?
C39 C34 C33 119.70(12) . . ?
C34 C35 C36 120.19(13) . . ?
C37 C36 C35 120.11(13) . . ?
C38 C37 C36 119.96(13) . . ?
C39 C38 C37 120.06(13) . . ?
C38 C39 C34 120.63(13) . . ?
C41 C40 B4 121.56(11) . . ?
C45 C40 C41 116.87(11) . . ?
C45 C40 B4 121.56(11) . . ?
C42 C41 C40 122.03(12) . . ?
C43 C42 C41 119.83(12) . . ?
C42 C43 C44 119.48(12) . . ?
C43 C44 C45 120.22(12) . . ?
C44 C45 C40 121.55(12) . . ?
C47 C46 C51 117.80(12) . . ?
C47 C46 B5 121.61(12) . . ?
C51 C46 B5 120.53(12) . . ?
C48 C47 C46 120.95(13) . . ?
C49 C48 C47 120.17(13) . . ?
C50 C49 C48 119.92(13) . . ?
C49 C50 C51 119.82(13) . . ?
C50 C51 C46 121.34(13) . . ?
C53 C52 B6 120.62(12) . . ?
C57 C52 C53 117.51(12) . . ?
C57 C52 B6 121.78(12) . . ?
C54 C53 C52 121.20(13) . . ?
C55 C54 C53 119.87(14) . . ?
C54 C55 C56 120.12(13) . . ?
C55 C56 C57 119.79(14) . . ?
C56 C57 C52 121.49(13) . . ?
O4 B4 O6 113.13(10) . . ?
O4 B4 N3 105.36(10) . . ?
O4 B4 C40 113.11(10) . . ?
O6 B4 N3 105.90(10) . . ?
O6 B4 C40 113.15(10) . . ?
C40 B4 N3 105.26(10) . . ?
O4 B5 O5 121.51(12) . . ?
O4 B5 C46 121.53(12) . . ?
O5 B5 C46 116.94(11) . . ?
O5 B6 C52 116.92(11) . . ?
O6 B6 O5 121.41(12) . . ?
O6 B6 C52 121.60(12) . . ?
N2 C26 C27 115.79(12) . . ?
C28 C27 C26 120.21(14) . . ?
C28 C27 C32 118.54(13) . . ?
C32 C27 C26 121.25(14) . . ?
C27 C28 C29 120.83(15) . . ?
C30 C29 C28 120.07(15) . . ?
C29 C30 C31 119.64(14) . . ?
C30 C31 C32 120.20(15) . . ?
C31 C32 C27 120.70(15) . . ?
N4 C58 C59 113.08(12) . . ?
C60 C59 C58 119.27(13) . . ?
C64 C59 C58 122.33(13) . . ?
C64 C59 C60 118.39(13) . . ?
C61 C60 C59 121.01(14) . . ?
C60 C61 C62 120.21(14) . . ?
C63 C62 C61 119.38(14) . . ?
C62 C63 C64 120.46(14) . . ?
C63 C64 C59 120.55(13) . . ?

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
N1 H1A N2 0.938(16) 2.058(17) 2.9956(17) 177.6(13) .
N3 H3B N4 0.936(18) 2.020(19) 2.9520(17) 173.7(16) .

_shelx_SHELXL_version_number     2014/7
####################################################################### 
# 
# 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_7a_14srv233
_database_code_depnum_ccdc_archive 'CCDC 1563949'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2017-07-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2016/6

_chemical_name_common            ?
_chemical_name_systematic        3,4,5-trifluorophenylboroxine
_chemical_formula_moiety         'C18 H6 B3 F9 O3'
_chemical_formula_sum            'C18 H6 B3 F9 O3'
_chemical_formula_weight         473.66
_chemical_melting_point          ?
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'
F F 0.0727 0.0534 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.8086(4)
_cell_length_b                   12.6262(4)
_cell_length_c                   12.8625(5)
_cell_angle_alpha                90
_cell_angle_beta                 119.598(2)
_cell_angle_gamma                90
_cell_volume                     1808.74(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3537
_cell_measurement_temperature    220
_cell_measurement_theta_max      75.088
_cell_measurement_theta_min      3.95
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.564
_exptl_absorpt_coefficient_mu    1.579
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.5487
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0927 after correction.
The Ratio of minimum to maximum transmission is 0.7278.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapetsoid
_exptl_crystal_F_000             936
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.0160
1.00 0.00 0.00 0.0630
-1.00 3.00 0.00 0.0830
1.00 0.00 -1.00 0.2010
1.00 1.00 0.00 0.0930
-1.00 -1.00 0.00 0.0750
1.00 -3.00 -1.00 0.1170
-1.00 3.00 1.00 0.1150
1.00 -3.00 0.00 0.0950
0.00 0.00 1.00 0.1410
0.00 0.00 -1.00 0.1540

_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.126
_exptl_special_details           
;
The data collection nominally covered full sphere of reciprocal 
space, by a combination of 7 runs of narrow-frame ω-scans (scan 
width 0.5° ω, 3s exposure for 3 low-θ runs, 6s for 4 high-θ runs), 
every run at a different 2θ and/or φ angle. Crystal to detector 
distance 3.50 cm.
Phase transition on cooling below 210 K.
;

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6438
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         75.320
_diffrn_reflns_theta_min         5.296
_diffrn_ambient_temperature      220
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Incoatec I\mS microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1418
_reflns_number_total             1790
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2016/6 multi-CPU (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      1.053
_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)+(0.1380P)²+0.0940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1811
_refine_ls_wR_factor_ref         0.1941
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.500000 1.24897(15) 0.250000 0.0848(6) Uani 1 2 d S T P . .
F2 F 0.44542(16) 1.14318(11) 0.39804(14) 0.0867(5) Uani 1 1 d . . . . .
F3 F 0.26021(14) 0.62852(13) 0.55967(14) 0.0839(5) Uani 1 1 d . . . . .
F4 F 0.23531(12) 0.41784(12) 0.53955(13) 0.0773(5) Uani 1 1 d . . . . .
F5 F 0.30137(15) 0.30961(11) 0.40274(15) 0.0851(5) Uani 1 1 d . . . . .
O1 O 0.45204(12) 0.74488(12) 0.30892(11) 0.0589(4) Uani 1 1 d . . . . .
O2 O 0.500000 0.58135(15) 0.250000 0.0553(5) Uani 1 2 d S T P . .
C1 C 0.500000 1.1430(2) 0.250000 0.0626(7) Uani 1 2 d S T P . .
C2 C 0.47108(19) 1.08739(18) 0.32481(19) 0.0622(5) Uani 1 1 d . . . . .
C3 C 0.46917(17) 0.97852(17) 0.32450(16) 0.0582(5) Uani 1 1 d . . . . .
H3 H 0.447147 0.941883 0.374358 0.070 Uiso 1 1 calc R . . . .
C4 C 0.500000 0.9225(2) 0.250000 0.0529(6) Uani 1 2 d S T P . .
C5 C 0.38451(16) 0.57557(15) 0.36404(16) 0.0534(5) Uani 1 1 d . . . . .
C6 C 0.34690(19) 0.63131(16) 0.43379(18) 0.0591(5) Uani 1 1 d . . . . .
H6 H 0.355898 0.705257 0.441460 0.071 Uiso 1 1 calc R . . . .
C7 C 0.29675(19) 0.57719(18) 0.49092(19) 0.0612(5) Uani 1 1 d . . . . .
C8 C 0.28253(17) 0.46934(18) 0.48158(18) 0.0601(6) Uani 1 1 d . . . . .
C9 C 0.31780(19) 0.41485(17) 0.41092(19) 0.0607(5) Uani 1 1 d . . . . .
C10 C 0.36906(17) 0.46612(16) 0.35295(17) 0.0564(5) Uani 1 1 d . . . . .
H10 H 0.393528 0.427596 0.306146 0.068 Uiso 1 1 calc R . . . .
B1 B 0.500000 0.7998(3) 0.250000 0.0554(7) Uani 1 2 d S T P . .
B2 B 0.44711(18) 0.63597(19) 0.30444(17) 0.0532(5) 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 C1 1.338(4) . ?
F2 C2 1.341(2) . ?
F3 C7 1.353(2) . ?
F4 C8 1.338(2) . ?
F5 C9 1.341(3) . ?
O1 B1 1.376(2) . ?
O1 B2 1.376(3) . ?
O2 B2 1.376(2) 2_655 ?
O2 B2 1.376(2) . ?
C1 C2 1.381(3) . ?
C1 C2 1.381(3) 2_655 ?
C2 C3 1.375(3) . ?
C3 C4 1.396(2) . ?
C4 B1 1.549(4) . ?
C5 C6 1.400(3) . ?
C5 C10 1.393(3) . ?
C5 B2 1.555(3) . ?
C6 C7 1.373(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.375(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
B1 O1 B2 120.29(17) . . ?
B2 O2 B2 119.8(2) . 2_655 ?
F1 C1 C2 120.54(14) . . ?
F1 C1 C2 120.54(14) . 2_655 ?
C2 C1 C2 118.9(3) . 2_655 ?
F2 C2 C1 117.8(2) . . ?
F2 C2 C3 121.15(18) . . ?
C3 C2 C1 121.10(19) . . ?
C2 C3 C4 119.88(18) . . ?
C3 C4 C3 119.1(3) . 2_655 ?
C3 C4 B1 120.46(13) . . ?
C3 C4 B1 120.46(13) 2_655 . ?
C6 C5 B2 119.59(18) . . ?
C10 C5 C6 119.20(17) . . ?
C10 C5 B2 121.17(17) . . ?
C7 C6 C5 119.53(19) . . ?
F3 C7 C6 121.05(19) . . ?
F3 C7 C8 117.33(18) . . ?
C8 C7 C6 121.61(18) . . ?
F4 C8 C7 120.72(19) . . ?
F4 C8 C9 120.6(2) . . ?
C7 C8 C9 118.66(18) . . ?
F5 C9 C8 117.08(18) . . ?
F5 C9 C10 121.49(19) . . ?
C10 C9 C8 121.4(2) . . ?
C9 C10 C5 119.56(18) . . ?
O1 B1 O1 119.4(3) . 2_655 ?
O1 B1 C4 120.28(13) 2_655 . ?
O1 B1 C4 120.28(13) . . ?
O1 B2 C5 119.56(17) . . ?
O2 B2 O1 119.87(17) . . ?
O2 B2 C5 120.5(2) . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
