# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1962509'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_1a                  
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.918 Check 
RESPONSE: Due to weak diffuse scattering around Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-10-29T16:21:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H11 B O2'
_chemical_formula_weight         246.06

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8170(2)
_cell_length_b                   4.72630(10)
_cell_length_c                   18.1904(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.366(2)
_cell_angle_gamma                90
_cell_volume                     1160.33(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10088
_cell_measurement_theta_min      2.476
_cell_measurement_theta_max      76.955

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.613
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.061
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 0 -2 0.0162
-6 2 -1 0.1888
0 -3 0 0.2969
-3 0 12 0.0525
3 0 -12 0.0505
-2 2 -9 0.1332
6 -2 -1 0.2426
5 -2 2 0.2365
9 0 -5 0.042
8 1 -6 0.0895
8 0 4 0.0386


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.957

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0857722
_diffrn_orient_matrix_ub_12      -0.1877262
_diffrn_orient_matrix_ub_13      0.0132861
_diffrn_orient_matrix_ub_21      0.020528
_diffrn_orient_matrix_ub_22      0.0945992
_diffrn_orient_matrix_ub_23      0.0829505
_diffrn_orient_matrix_ub_31      -0.0724333
_diffrn_orient_matrix_ub_32      0.2491238
_diffrn_orient_matrix_ub_33      -0.0215219
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.05
_diffrn_reflns_number            19552
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.274
_diffrn_reflns_theta_max         77.519
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_reflns_Friedel_coverage         0
_reflns_number_total             2402
_reflns_number_gt                2218
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.4848P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2402
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Inconsistent reflections -7 3 4 and -7 3 6 were omitted.
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 0.0039 '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'

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 0.17994(6) 0.42199(18) 0.30652(5) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.33331(6) 0.47150(18) 0.26534(4) 0.0210(2) Uani 1 1 d . . . . .
C1 C 0.22097(9) 0.2165(3) 0.35800(6) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.32069(9) 0.1374(3) 0.36256(6) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.37720(9) 0.2644(3) 0.31528(6) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.47291(9) 0.1856(3) 0.31791(7) 0.0227(3) Uani 1 1 d . . . . .
H4 H 0.509948 0.271829 0.285591 0.027 Uiso 1 1 calc R U . . .
C5 C 0.51610(9) -0.0263(3) 0.36953(7) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.582648 -0.082197 0.371499 0.029 Uiso 1 1 calc R U . . .
C6 C 0.46407(9) -0.1526(3) 0.41669(7) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.494968 -0.293558 0.451061 0.028 Uiso 1 1 calc R U . . .
C7 C 0.36448(9) -0.0749(3) 0.41467(6) 0.0206(3) Uani 1 1 d . . . . .
C8 C 0.30535(9) -0.1981(3) 0.46125(7) 0.0231(3) Uani 1 1 d . . . . .
H8 H 0.333061 -0.337947 0.497141 0.028 Uiso 1 1 calc R U . . .
C9 C 0.20887(9) -0.1169(3) 0.45479(7) 0.0237(3) Uani 1 1 d . . . . .
H9 H 0.170357 -0.203492 0.486006 0.028 Uiso 1 1 calc R U . . .
C10 C 0.16510(9) 0.0929(3) 0.40276(7) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.097998 0.147051 0.398969 0.027 Uiso 1 1 calc R U . . .
C11 C 0.18847(8) 0.7776(3) 0.20379(6) 0.0196(3) Uani 1 1 d . . . . .
C12 C 0.24351(9) 0.9080(3) 0.15703(7) 0.0217(3) Uani 1 1 d . . . . .
H12 H 0.310966 0.856916 0.161187 0.026 Uiso 1 1 calc R U . . .
C13 C 0.20121(9) 1.1110(3) 0.10461(7) 0.0237(3) Uani 1 1 d . . . . .
H13 H 0.239615 1.197162 0.073254 0.028 Uiso 1 1 calc R U . . .
C14 C 0.10280(9) 1.1874(3) 0.09815(7) 0.0243(3) Uani 1 1 d . . . . .
H14 H 0.073691 1.325377 0.062172 0.029 Uiso 1 1 calc R U . . .
C15 C 0.04679(9) 1.0623(3) 0.14429(7) 0.0239(3) Uani 1 1 d . . . . .
H15 H -0.020453 1.115672 0.140146 0.029 Uiso 1 1 calc R U . . .
C16 C 0.08935(9) 0.8590(3) 0.19652(7) 0.0223(3) Uani 1 1 d . . . . .
H16 H 0.050602 0.773888 0.227786 0.027 Uiso 1 1 calc R U . . .
B1 B 0.23615(10) 0.5457(3) 0.26134(7) 0.0199(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3762(16) . ?
O1 C1 1.3836(14) . ?
O2 B1 1.3743(16) . ?
O2 C3 1.3839(14) . ?
C1 C10 1.3673(17) . ?
C1 C2 1.4127(16) . ?
C2 C3 1.4130(17) . ?
C2 C7 1.4235(16) . ?
C3 C4 1.3647(17) . ?
C4 C5 1.4147(17) . ?
C4 H4 0.95 . ?
C5 C6 1.3687(18) . ?
C5 H5 0.95 . ?
C6 C7 1.4170(17) . ?
C6 H6 0.95 . ?
C7 C8 1.4216(17) . ?
C8 C9 1.3679(18) . ?
C8 H8 0.95 . ?
C9 C10 1.4141(17) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.3996(17) . ?
C11 C16 1.4013(16) . ?
C11 B1 1.5606(18) . ?
C12 C13 1.3901(17) . ?
C12 H12 0.95 . ?
C13 C14 1.3873(18) . ?
C13 H13 0.95 . ?
C14 C15 1.3895(18) . ?
C14 H14 0.95 . ?
C15 C16 1.3902(17) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?

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 C1 120.03(10) . . ?
B1 O2 C3 120.07(10) . . ?
C10 C1 O1 120.08(11) . . ?
C10 C1 C2 121.33(11) . . ?
O1 C1 C2 118.59(10) . . ?
C1 C2 C3 120.73(11) . . ?
C1 C2 C7 119.72(11) . . ?
C3 C2 C7 119.55(11) . . ?
C4 C3 O2 120.06(11) . . ?
C4 C3 C2 121.36(11) . . ?
O2 C3 C2 118.57(10) . . ?
C3 C4 C5 118.96(11) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.42(11) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.54(11) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 123.86(11) . . ?
C6 C7 C2 118.16(11) . . ?
C8 C7 C2 117.98(11) . . ?
C9 C8 C7 120.51(11) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.57(11) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C9 118.89(11) . . ?
C1 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C16 117.96(11) . . ?
C12 C11 B1 120.71(11) . . ?
C16 C11 B1 121.33(11) . . ?
C13 C12 C11 121.16(11) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 119.89(11) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.04(11) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C14 C15 C16 119.87(11) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.08(11) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
O2 B1 O1 121.99(11) . . ?
O2 B1 C11 118.82(11) . . ?
O1 B1 C11 119.19(11) . . ?

####################################################################### 
# 
# 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_16a
_database_code_depnum_ccdc_archive 'CCDC 1965596'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT088_16a                 
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.35 Note  
RESPONSE: Due to the entire structure being positionally disordered.
;
_vrf_PLAT906_16a                 
;
PROBLEM: Large K Value in the Analysis of Variance ......      5.301 Check 
RESPONSE: Due to weak high angle data.
;
_vrf_PLAT911_16a                 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2019-11-13T10:02:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H12 B2 O4'
_chemical_formula_weight         337.92

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3335(2)
_cell_length_b                   5.12500(10)
_cell_length_c                   12.2086(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.641(2)
_cell_angle_gamma                90
_cell_volume                     758.43(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4368
_cell_measurement_theta_min      3.625
_cell_measurement_theta_max      75.976

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       blade
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.009
_exptl_crystal_density_diffrn    1.48
_exptl_crystal_F_000             348
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0071
-1 0 0 0.0017
0 -2 1 0.0374
0 2 -1 0.0337
0 -2 -1 0.0226
-2 0 8 0.0657
0 3 0 0.0386
1 1 -8 0.0887


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.993

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0044137
_diffrn_orient_matrix_ub_12      0.0688769
_diffrn_orient_matrix_ub_13      0.1218865
_diffrn_orient_matrix_ub_21      -0.126957
_diffrn_orient_matrix_ub_22      -0.006059
_diffrn_orient_matrix_ub_23      -0.0275002
_diffrn_orient_matrix_ub_31      0.0016009
_diffrn_orient_matrix_ub_32      -0.2927434
_diffrn_orient_matrix_ub_33      0.02932
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_number            10355
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.646
_diffrn_reflns_theta_max         76.776
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_reflns_Friedel_coverage         0
_reflns_number_total             1559
_reflns_number_gt                1403
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.2620P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1559
_refine_ls_number_parameters     212
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;In this structure the entire molecule was disordered over two positions with
 site occupancies of 0.92 and 0.08 for PART 1 and PART 2, respectively. To help
 maintain reasonable ADP values for the minor component, RIGU and SIMU 
 restraints were applied. Inconsistent reflections 1 0 8 and 3 3 8 were omitted.,Positional disorder of all atoms within the structure.
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 0.0039 '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'

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 0.35453(8) 0.0867(2) 0.41858(8) 0.0215(3) Uani 0.925(2) 1 d . U P A 1
O2 O 0.45718(8) 0.2956(2) 0.58122(8) 0.0216(3) Uani 0.925(2) 1 d . U P A 1
C1 C 0.26609(12) 0.2533(3) 0.41825(13) 0.0198(3) Uani 0.925(2) 1 d . . P A 1
C2 C 0.27444(13) 0.4468(3) 0.50212(12) 0.0200(3) Uani 0.925(2) 1 d . . P A 1
C3 C 0.37116(13) 0.4677(3) 0.58462(13) 0.0207(3) Uani 0.925(2) 1 d . . P A 1
C4 C 0.38097(15) 0.6512(4) 0.66689(14) 0.0241(4) Uani 0.925(2) 1 d . . P A 1
H4 H 0.4466 0.663743 0.721334 0.029 Uiso 0.925(2) 1 calc R U P A 1
C5 C 0.29164(15) 0.8220(4) 0.66949(16) 0.0272(4) Uani 0.925(2) 1 d . . P A 1
H5 H 0.297586 0.949583 0.726729 0.033 Uiso 0.925(2) 1 calc R U P A 1
C6 C 0.19670(15) 0.8078(4) 0.59140(14) 0.0256(4) Uani 0.925(2) 1 d . . P A 1
H6 H 0.137832 0.925057 0.595195 0.031 Uiso 0.925(2) 1 calc R U P A 1
C7 C 0.18543(13) 0.6195(3) 0.50476(13) 0.0223(4) Uani 0.925(2) 1 d . . P A 1
C8 C 0.08970(14) 0.5918(4) 0.42021(14) 0.0253(4) Uani 0.925(2) 1 d . . P A 1
H8 H 0.02884 0.706066 0.41903 0.03 Uiso 0.925(2) 1 calc R U P A 1
C9 C 0.08476(14) 0.4010(4) 0.34033(15) 0.0254(4) Uani 0.925(2) 1 d . . P A 1
H9 H 0.019921 0.384917 0.285045 0.03 Uiso 0.925(2) 1 calc R U P A 1
C10 C 0.17329(14) 0.2286(4) 0.33829(14) 0.0228(4) Uani 0.925(2) 1 d . . P A 1
H10 H 0.168577 0.097893 0.282447 0.027 Uiso 0.925(2) 1 calc R U P A 1
B1 B 0.44720(13) 0.1063(3) 0.50007(13) 0.0214(3) Uani 0.925(2) 1 d . U P A 1
O3 O 0.1447(12) 0.912(3) 0.5834(11) 0.028(3) Uani 0.075(2) 1 d . U P A 2
O4 O 0.0407(11) 0.712(3) 0.4192(11) 0.030(3) Uani 0.075(2) 1 d . U P A 2
B2 B 0.0516(18) 0.889(4) 0.5013(19) 0.029(4) Uani 0.075(2) 1 d . U P A 2
C11 C 0.2291(11) 0.748(2) 0.5818(11) 0.019(3) Uani 0.075(2) 1 d G U P A 2
C12 C 0.3246(12) 0.769(3) 0.6621(10) 0.016(4) Uani 0.075(2) 1 d G U P A 2
H12 H 0.330054 0.89909 0.718126 0.019 Uiso 0.075(2) 1 calc R U P A 2
C13 C 0.4121(10) 0.599(3) 0.6604(10) 0.024(3) Uani 0.075(2) 1 d G U P A 2
H13 H 0.477327 0.612879 0.71526 0.028 Uiso 0.075(2) 1 calc R U P A 2
C14 C 0.4041(9) 0.408(3) 0.5784(10) 0.018(3) Uani 0.075(2) 1 d G U P A 2
H14 H 0.463894 0.291538 0.577247 0.022 Uiso 0.075(2) 1 calc R U P A 2
C15 C 0.3086(8) 0.387(2) 0.4981(8) 0.021(3) Uani 0.075(2) 1 d G U P A 2
C16 C 0.2212(8) 0.557(2) 0.4998(8) 0.015(3) Uani 0.075(2) 1 d G U P A 2
C17 C 0.1257(9) 0.536(3) 0.4196(11) 0.022(3) Uani 0.075(2) 1 d G U P A 2
C18 C 0.1177(11) 0.345(3) 0.3376(11) 0.022(4) Uani 0.075(2) 1 d G U P A 2
H18 H 0.05247 0.330885 0.282706 0.027 Uiso 0.075(2) 1 calc R U P A 2
C19 C 0.2052(12) 0.175(3) 0.3359(11) 0.025(3) Uani 0.075(2) 1 d G U P A 2
H19 H 0.199739 0.044668 0.279835 0.03 Uiso 0.075(2) 1 calc R U P A 2
C20 C 0.3007(11) 0.196(2) 0.4161(11) 0.019(3) Uani 0.075(2) 1 d G U P A 2
H20 H 0.360447 0.079786 0.414979 0.023 Uiso 0.075(2) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3734(18) . ?
O1 C1 1.3847(18) . ?
O2 B1 1.3756(19) . ?
O2 C3 1.3862(18) . ?
C1 C10 1.366(2) . ?
C1 C2 1.415(2) . ?
C2 C7 1.415(2) . ?
C2 C3 1.416(2) . ?
C3 C4 1.365(2) . ?
C4 C5 1.412(2) . ?
C4 H4 0.95 . ?
C5 C6 1.369(2) . ?
C5 H5 0.95 . ?
C6 C7 1.420(2) . ?
C6 H6 0.95 . ?
C7 C8 1.425(2) . ?
C8 C9 1.375(2) . ?
C8 H8 0.95 . ?
C9 C10 1.408(2) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
B1 B1 1.699(3) 3_656 ?
O3 C11 1.343(18) . ?
O3 B2 1.38(3) . ?
O4 B2 1.34(3) . ?
O4 C17 1.383(18) . ?
B2 B2 1.70(4) 3_576 ?
C11 C12 1.39 . ?
C11 C16 1.39 . ?
C12 C13 1.39 . ?
C12 H12 0.95 . ?
C13 C14 1.39 . ?
C13 H13 0.95 . ?
C14 C15 1.39 . ?
C14 H14 0.95 . ?
C15 C16 1.39 . ?
C15 C20 1.39 . ?
C16 C17 1.39 . ?
C17 C18 1.39 . ?
C18 C19 1.39 . ?
C18 H18 0.95 . ?
C19 C20 1.39 . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?

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 C1 120.43(12) . . ?
B1 O2 C3 120.19(12) . . ?
C10 C1 O1 120.04(14) . . ?
C10 C1 C2 121.41(14) . . ?
O1 C1 C2 118.55(13) . . ?
C7 C2 C1 120.09(13) . . ?
C7 C2 C3 119.45(14) . . ?
C1 C2 C3 120.45(14) . . ?
C4 C3 O2 119.74(14) . . ?
C4 C3 C2 121.61(14) . . ?
O2 C3 C2 118.65(13) . . ?
C3 C4 C5 118.69(15) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.49(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.55(16) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 118.20(14) . . ?
C2 C7 C8 117.65(15) . . ?
C6 C7 C8 124.15(15) . . ?
C9 C8 C7 120.47(16) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.73(15) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C1 C10 C9 118.64(15) . . ?
C1 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
O1 B1 O2 121.69(13) . . ?
O1 B1 B1 119.20(16) . 3_656 ?
O2 B1 B1 119.11(16) . 3_656 ?
C11 O3 B2 118.6(14) . . ?
B2 O4 C17 117.9(14) . . ?
O4 B2 O3 123.7(18) . . ?
O4 B2 B2 118(2) . 3_576 ?
O3 B2 B2 118(2) . 3_576 ?
O3 C11 C12 120.0(9) . . ?
O3 C11 C16 120.0(9) . . ?
C12 C11 C16 120 . . ?
C11 C12 C13 120 . . ?
C11 C12 H12 120 . . ?
C13 C12 H12 120 . . ?
C14 C13 C12 120 . . ?
C14 C13 H13 120 . . ?
C12 C13 H13 120 . . ?
C15 C14 C13 120 . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C14 C15 C16 120 . . ?
C14 C15 C20 120 . . ?
C16 C15 C20 120 . . ?
C15 C16 C17 120 . . ?
C15 C16 C11 120 . . ?
C17 C16 C11 120 . . ?
O4 C17 C18 120.3(9) . . ?
O4 C17 C16 119.7(9) . . ?
C18 C17 C16 120 . . ?
C17 C18 C19 120 . . ?
C17 C18 H18 120 . . ?
C19 C18 H18 120 . . ?
C20 C19 C18 120 . . ?
C20 C19 H19 120 . . ?
C18 C19 H19 120 . . ?
C19 C20 C15 120 . . ?
C19 C20 H20 120 . . ?
C15 C20 H20 120 . . ?


# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1962515'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_10a                 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2019-06-13T14:38:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C11 H9 B O3'
_chemical_formula_weight         199.99

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.9961(2)
_cell_length_b                   8.76840(10)
_cell_length_c                   14.2648(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.7300(10)
_cell_angle_gamma                90
_cell_volume                     2805.64(6)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20621
_cell_measurement_theta_min      5.376
_cell_measurement_theta_max      77.067

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.017
_exptl_crystal_density_diffrn    1.42
_exptl_crystal_F_000             1248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 -8 0.0613
-1 4 -5 0.0748
0 4 6 0.0455
1 -5 5 0.045
15 0 -4 0.0088
-15 0 4 0.0083


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.9
_shelx_estimated_absorpt_T_max   0.986

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0230863
_diffrn_orient_matrix_ub_12      -0.1087974
_diffrn_orient_matrix_ub_13      -0.0848367
_diffrn_orient_matrix_ub_21      -0.0627594
_diffrn_orient_matrix_ub_22      0.0054962
_diffrn_orient_matrix_ub_23      0.0215379
_diffrn_orient_matrix_ub_31      -0.0157388
_diffrn_orient_matrix_ub_32      0.137828
_diffrn_orient_matrix_ub_33      -0.0677618
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_number            36569
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.941
_diffrn_reflns_theta_max         77.381
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_reflns_Friedel_coverage         0
_reflns_number_total             5830
_reflns_number_gt                5091
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.6417P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5830
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.094
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 0.0039 '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'

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 0.48843(3) 0.72807(8) 0.43677(5) 0.01870(16) Uani 1 1 d . . . . .
O2 O 0.51025(3) 0.79707(8) 0.60467(5) 0.01934(16) Uani 1 1 d . . . . .
O3 O 0.56122(3) 0.91499(9) 0.50176(5) 0.02135(17) Uani 1 1 d . . . . .
O4 O 0.80835(3) 0.98279(9) 0.44281(5) 0.02053(17) Uani 1 1 d . . . . .
O5 O 0.74941(3) 0.75768(9) 0.39025(6) 0.02219(17) Uani 1 1 d . . . . .
O6 O 0.70771(3) 0.99607(9) 0.35579(6) 0.02313(18) Uani 1 1 d . . . . .
O7 O 0.86066(3) 0.63156(9) 0.23330(5) 0.02111(17) Uani 1 1 d . . . . .
O8 O 0.92022(3) 0.40224(9) 0.26470(6) 0.02229(17) Uani 1 1 d . . . . .
O9 O 0.96397(3) 0.63582(9) 0.30661(6) 0.02303(17) Uani 1 1 d . . . . .
C1 C 0.44538(4) 0.62595(12) 0.45072(7) 0.0169(2) Uani 1 1 d . . . . .
C2 C 0.43470(4) 0.60988(12) 0.54406(7) 0.0173(2) Uani 1 1 d . . . . .
C3 C 0.46806(5) 0.69527(12) 0.62162(8) 0.0184(2) Uani 1 1 d . . . . .
C4 C 0.45968(5) 0.67747(13) 0.71274(8) 0.0220(2) Uani 1 1 d . . . . .
H4 H 0.482312 0.735848 0.764152 0.026 Uiso 1 1 calc R U . . .
C5 C 0.41700(5) 0.57133(13) 0.72977(8) 0.0243(2) Uani 1 1 d . . . . .
H5 H 0.411426 0.558137 0.793304 0.029 Uiso 1 1 calc R U . . .
C6 C 0.38343(5) 0.48688(13) 0.65652(8) 0.0233(2) Uani 1 1 d . . . . .
H6 H 0.354722 0.416806 0.669611 0.028 Uiso 1 1 calc R U . . .
C7 C 0.39144(5) 0.50386(12) 0.56099(8) 0.0194(2) Uani 1 1 d . . . . .
C8 C 0.35984(5) 0.41741(13) 0.48173(8) 0.0218(2) Uani 1 1 d . . . . .
H8 H 0.330339 0.346473 0.490804 0.026 Uiso 1 1 calc R U . . .
C9 C 0.37159(5) 0.43559(13) 0.39226(8) 0.0220(2) Uani 1 1 d . . . . .
H9 H 0.350243 0.376006 0.340322 0.026 Uiso 1 1 calc R U . . .
C10 C 0.41470(5) 0.54087(13) 0.37543(8) 0.0202(2) Uani 1 1 d . . . . .
H10 H 0.422261 0.552383 0.312971 0.024 Uiso 1 1 calc R U . . .
C11 C 0.57870(5) 0.92741(13) 0.41118(8) 0.0244(2) Uani 1 1 d . . . . .
H11A H 0.589702 0.826451 0.391232 0.037 Uiso 1 1 calc R U . . .
H11B H 0.612922 0.99635 0.418089 0.037 Uiso 1 1 calc R U . . .
H11C H 0.545366 0.967886 0.362546 0.037 Uiso 1 1 calc R U . . .
C12 C 0.85722(5) 0.89360(13) 0.48190(7) 0.0193(2) Uani 1 1 d . . . . .
C13 C 0.85205(5) 0.73338(13) 0.47334(7) 0.0192(2) Uani 1 1 d . . . . .
C14 C 0.79765(5) 0.66479(13) 0.42695(8) 0.0200(2) Uani 1 1 d . . . . .
C15 C 0.79228(5) 0.51040(13) 0.41650(8) 0.0242(2) Uani 1 1 d . . . . .
H15 H 0.755396 0.466025 0.385325 0.029 Uiso 1 1 calc R U . . .
C16 C 0.84236(5) 0.41758(13) 0.45271(9) 0.0265(2) Uani 1 1 d . . . . .
H16 H 0.83892 0.310082 0.445203 0.032 Uiso 1 1 calc R U . . .
C17 C 0.89587(5) 0.47939(14) 0.49848(8) 0.0255(2) Uani 1 1 d . . . . .
H17 H 0.928901 0.414518 0.522322 0.031 Uiso 1 1 calc R U . . .
C18 C 0.90223(5) 0.63975(13) 0.51049(8) 0.0214(2) Uani 1 1 d . . . . .
C19 C 0.95618(5) 0.71152(14) 0.55710(8) 0.0249(2) Uani 1 1 d . . . . .
H19 H 0.990279 0.651401 0.583145 0.03 Uiso 1 1 calc R U . . .
C20 C 0.95926(5) 0.86728(14) 0.56467(8) 0.0253(2) Uani 1 1 d . . . . .
H20 H 0.995682 0.913443 0.596302 0.03 Uiso 1 1 calc R U . . .
C21 C 0.90966(5) 0.96104(14) 0.52665(8) 0.0234(2) Uani 1 1 d . . . . .
H21 H 0.91268 1.068878 0.532069 0.028 Uiso 1 1 calc R U . . .
C22 C 0.70940(5) 1.15957(13) 0.36015(9) 0.0272(3) Uani 1 1 d . . . . .
H22A H 0.740949 1.197247 0.329856 0.041 Uiso 1 1 calc R U . . .
H22B H 0.717512 1.192401 0.427449 0.041 Uiso 1 1 calc R U . . .
H22C H 0.670896 1.200712 0.326115 0.041 Uiso 1 1 calc R U . . .
C23 C 0.81066(5) 0.54621(13) 0.19385(8) 0.0202(2) Uani 1 1 d . . . . .
C24 C 0.81598(5) 0.38569(13) 0.19102(7) 0.0206(2) Uani 1 1 d . . . . .
C25 C 0.87132(5) 0.31329(13) 0.22746(8) 0.0215(2) Uani 1 1 d . . . . .
C26 C 0.87716(6) 0.15864(14) 0.22642(9) 0.0282(3) Uani 1 1 d . . . . .
H26 H 0.914697 0.111936 0.251035 0.034 Uiso 1 1 calc R U . . .
C27 C 0.82655(6) 0.06918(15) 0.18819(10) 0.0329(3) Uani 1 1 d . . . . .
H27 H 0.830239 -0.038703 0.187447 0.04 Uiso 1 1 calc R U . . .
C28 C 0.77222(6) 0.13474(15) 0.15212(9) 0.0317(3) Uani 1 1 d . . . . .
H28 H 0.73886 0.071892 0.126426 0.038 Uiso 1 1 calc R U . . .
C29 C 0.76511(5) 0.29549(14) 0.15266(8) 0.0247(2) Uani 1 1 d . . . . .
C30 C 0.70992(5) 0.37165(16) 0.11851(8) 0.0295(3) Uani 1 1 d . . . . .
H30 H 0.675084 0.313954 0.092826 0.035 Uiso 1 1 calc R U . . .
C31 C 0.70650(5) 0.52732(16) 0.12229(9) 0.0299(3) Uani 1 1 d . . . . .
H31 H 0.669161 0.575872 0.099154 0.036 Uiso 1 1 calc R U . . .
C32 C 0.75727(5) 0.61753(15) 0.15984(8) 0.0260(2) Uani 1 1 d . . . . .
H32 H 0.754357 0.725536 0.16141 0.031 Uiso 1 1 calc R U . . .
C33 C 0.96203(5) 0.79870(13) 0.31267(9) 0.0262(2) Uani 1 1 d . . . . .
H33A H 0.953157 0.842139 0.247779 0.039 Uiso 1 1 calc R U . . .
H33B H 1.000703 0.836679 0.348247 0.039 Uiso 1 1 calc R U . . .
H33C H 0.930901 0.828744 0.346143 0.039 Uiso 1 1 calc R U . . .
B1 B 0.51962(5) 0.81248(14) 0.51318(9) 0.0183(2) Uani 1 1 d . . . . .
B2 B 0.75580(5) 0.91361(14) 0.39716(9) 0.0198(2) Uani 1 1 d . . . . .
B3 B 0.91412(5) 0.55795(15) 0.26763(9) 0.0202(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3804(14) . ?
O1 C1 1.3813(12) . ?
O2 B1 1.3754(14) . ?
O2 C3 1.3785(13) . ?
O3 B1 1.3485(14) . ?
O3 C11 1.4394(13) . ?
O4 B2 1.3805(14) . ?
O4 C12 1.3818(13) . ?
O5 B2 1.3764(15) . ?
O5 C14 1.3827(13) . ?
O6 B2 1.3441(15) . ?
O6 C22 1.4351(13) . ?
O7 B3 1.3793(14) . ?
O7 C23 1.3833(13) . ?
O8 B3 1.3741(15) . ?
O8 C25 1.3755(13) . ?
O9 B3 1.3449(14) . ?
O9 C33 1.4321(14) . ?
C1 C10 1.3688(15) . ?
C1 C2 1.4133(14) . ?
C2 C3 1.4139(15) . ?
C2 C7 1.4204(15) . ?
C3 C4 1.3642(15) . ?
C4 C5 1.4120(17) . ?
C4 H4 0.95 . ?
C5 C6 1.3714(17) . ?
C5 H5 0.95 . ?
C6 C7 1.4226(15) . ?
C6 H6 0.95 . ?
C7 C8 1.4210(16) . ?
C8 C9 1.3709(16) . ?
C8 H8 0.95 . ?
C9 C10 1.4134(16) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 C21 1.3682(15) . ?
C12 C13 1.4130(15) . ?
C13 C14 1.4142(15) . ?
C13 C18 1.4201(15) . ?
C14 C15 1.3646(16) . ?
C15 C16 1.4119(16) . ?
C15 H15 0.95 . ?
C16 C17 1.3710(17) . ?
C16 H16 0.95 . ?
C17 C18 1.4202(17) . ?
C17 H17 0.95 . ?
C18 C19 1.4191(16) . ?
C19 C20 1.3706(17) . ?
C19 H19 0.95 . ?
C20 C21 1.4136(16) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 C32 1.3679(15) . ?
C23 C24 1.4141(16) . ?
C24 C25 1.4147(16) . ?
C24 C29 1.4182(15) . ?
C25 C26 1.3631(16) . ?
C26 C27 1.4097(17) . ?
C26 H26 0.95 . ?
C27 C28 1.3687(19) . ?
C27 H27 0.95 . ?
C28 C29 1.4192(18) . ?
C28 H28 0.95 . ?
C29 C30 1.4218(17) . ?
C30 C31 1.3691(19) . ?
C30 H30 0.95 . ?
C31 C32 1.4143(17) . ?
C31 H31 0.95 . ?
C32 H32 0.95 . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C33 H33C 0.98 . ?

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 C1 119.87(9) . . ?
B1 O2 C3 119.57(8) . . ?
B1 O3 C11 120.32(9) . . ?
B2 O4 C12 119.43(9) . . ?
B2 O5 C14 119.61(9) . . ?
B2 O6 C22 120.43(9) . . ?
B3 O7 C23 119.16(9) . . ?
B3 O8 C25 119.66(9) . . ?
B3 O9 C33 119.75(9) . . ?
C10 C1 O1 120.14(9) . . ?
C10 C1 C2 121.22(10) . . ?
O1 C1 C2 118.63(9) . . ?
C1 C2 C3 120.49(10) . . ?
C1 C2 C7 119.94(10) . . ?
C3 C2 C7 119.54(10) . . ?
C4 C3 O2 119.59(10) . . ?
C4 C3 C2 121.25(10) . . ?
O2 C3 C2 119.16(9) . . ?
C3 C4 C5 119.26(10) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.39(10) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.22(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C8 117.93(10) . . ?
C2 C7 C6 118.34(10) . . ?
C8 C7 C6 123.70(10) . . ?
C9 C8 C7 120.50(10) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.57(10) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C9 118.83(10) . . ?
C1 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C12 O4 119.90(10) . . ?
C21 C12 C13 121.25(10) . . ?
O4 C12 C13 118.84(9) . . ?
C12 C13 C14 120.81(10) . . ?
C12 C13 C18 119.77(10) . . ?
C14 C13 C18 119.41(10) . . ?
C15 C14 O5 119.82(10) . . ?
C15 C14 C13 121.49(10) . . ?
O5 C14 C13 118.68(9) . . ?
C14 C15 C16 119.02(11) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 121.36(11) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.44(10) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C13 118.23(10) . . ?
C19 C18 C17 123.49(10) . . ?
C13 C18 C17 118.27(10) . . ?
C20 C19 C18 120.23(10) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 121.73(10) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C12 C21 C20 118.77(11) . . ?
C12 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C32 C23 O7 119.84(10) . . ?
C32 C23 C24 121.43(10) . . ?
O7 C23 C24 118.73(9) . . ?
C23 C24 C25 120.84(10) . . ?
C23 C24 C29 119.80(10) . . ?
C25 C24 C29 119.35(11) . . ?
C26 C25 O8 119.62(10) . . ?
C26 C25 C24 121.69(11) . . ?
O8 C25 C24 118.69(10) . . ?
C25 C26 C27 118.87(11) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C28 C27 C26 121.28(12) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C27 C28 C29 120.78(11) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C24 C29 C28 118.02(11) . . ?
C24 C29 C30 117.93(11) . . ?
C28 C29 C30 124.04(11) . . ?
C31 C30 C29 120.63(11) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 121.52(11) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C23 C32 C31 118.69(11) . . ?
C23 C32 H32 120.7 . . ?
C31 C32 H32 120.7 . . ?
O9 C33 H33A 109.5 . . ?
O9 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O9 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O3 B1 O2 116.34(10) . . ?
O3 B1 O1 121.40(10) . . ?
O2 B1 O1 122.26(10) . . ?
O6 B2 O5 116.01(10) . . ?
O6 B2 O4 121.39(10) . . ?
O5 B2 O4 122.60(10) . . ?
O9 B3 O8 115.70(10) . . ?
O9 B3 O7 121.41(10) . . ?
O8 B3 O7 122.90(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_4a
_database_code_depnum_ccdc_archive 'CCDC 1962512'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_date             2019-04-30T12:43:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H8 B F3 O2'
_chemical_formula_weight         300.03

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.68950(10)
_cell_length_b                   4.72070(10)
_cell_length_c                   18.1961(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.4210(10)
_cell_angle_gamma                90
_cell_volume                     1232.27(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17518
_cell_measurement_theta_min      3.041
_cell_measurement_theta_max      76.69

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       blade
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 0 4 0.045
-8 0 -4 0.0648
4 -2 7 0.1236
-6 0 11 0.0479
-5 0 -9 0.0394
5 0 9 0.0379
-3 3 -5 0.1778
8 -1 5 0.0488
-9 -1 2 0.1023
7 0 -10 0.0455
1 1 -11 0.0866
2 0 -12 0.0228
-2 0 12 0.0371
1 0 11 0.0359
-1 0 -11 0.0266
2 0 11 0.0353


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.48a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.213
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.61
_shelx_estimated_absorpt_T_max   0.933

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0389347
_diffrn_orient_matrix_ub_12      -0.2703978
_diffrn_orient_matrix_ub_13      -0.0428695
_diffrn_orient_matrix_ub_21      0.0802218
_diffrn_orient_matrix_ub_22      0.0049025
_diffrn_orient_matrix_ub_23      -0.0423533
_diffrn_orient_matrix_ub_31      0.0598465
_diffrn_orient_matrix_ub_32      -0.1826202
_diffrn_orient_matrix_ub_33      0.062321
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_number            32221
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         77.543
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             2579
_reflns_number_gt                2410
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+0.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2579
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 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'

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 0.67007(4) 0.86067(15) 0.83958(4) 0.02681(18) Uani 1 1 d . . . . .
F2 F 0.93569(5) 1.37229(15) 0.94918(4) 0.03119(19) Uani 1 1 d . . . . .
F3 F 0.95615(4) 0.68890(15) 0.76956(4) 0.03067(19) Uani 1 1 d . . . . .
O1 O 0.81340(5) 0.40035(16) 0.69540(4) 0.02197(19) Uani 1 1 d . . . . .
O2 O 0.66996(5) 0.45349(16) 0.73685(4) 0.02087(19) Uani 1 1 d . . . . .
C1 C 0.80852(7) 0.7568(2) 0.79824(6) 0.0197(2) Uani 1 1 d . . . . .
C2 C 0.76145(7) 0.9120(2) 0.84402(6) 0.0205(2) Uani 1 1 d . . . . .
C3 C 0.80089(7) 1.1181(2) 0.89495(6) 0.0227(2) Uani 1 1 d . . . . .
H3 H 0.765469 1.217643 0.924564 0.027 Uiso 1 1 calc R U . . .
C4 C 0.89451(8) 1.1716(2) 0.90047(6) 0.0233(2) Uani 1 1 d . . . . .
C5 C 0.94781(7) 1.0321(2) 0.85852(6) 0.0241(2) Uani 1 1 d . . . . .
H5 H 1.012111 1.073299 0.863241 0.029 Uiso 1 1 calc R U . . .
C6 C 0.90298(7) 0.8284(2) 0.80902(6) 0.0222(2) Uani 1 1 d . . . . .
C7 C 0.77440(7) 0.1965(2) 0.64361(6) 0.0210(2) Uani 1 1 d . . . . .
C8 C 0.67998(7) 0.1213(2) 0.63852(6) 0.0197(2) Uani 1 1 d . . . . .
C9 C 0.62743(7) 0.2502(2) 0.68574(6) 0.0201(2) Uani 1 1 d . . . . .
C10 C 0.53654(7) 0.1786(2) 0.68229(6) 0.0227(2) Uani 1 1 d . . . . .
H10 H 0.50189 0.267278 0.714348 0.027 Uiso 1 1 calc R U . . .
C11 C 0.49502(7) -0.0307(2) 0.62997(6) 0.0246(2) Uani 1 1 d . . . . .
H11 H 0.431989 -0.083068 0.627499 0.029 Uiso 1 1 calc R U . . .
C12 C 0.54350(8) -0.1592(2) 0.58285(6) 0.0245(2) Uani 1 1 d . . . . .
H12 H 0.513605 -0.29777 0.548023 0.029 Uiso 1 1 calc R U . . .
C13 C 0.63796(7) -0.0877(2) 0.58552(6) 0.0215(2) Uani 1 1 d . . . . .
C14 C 0.69320(8) -0.2122(2) 0.53906(6) 0.0250(2) Uani 1 1 d . . . . .
H14 H 0.666607 -0.35022 0.502746 0.03 Uiso 1 1 calc R U . . .
C15 C 0.78476(8) -0.1349(2) 0.54619(6) 0.0257(2) Uani 1 1 d . . . . .
H15 H 0.820756 -0.221876 0.514873 0.031 Uiso 1 1 calc R U . . .
C16 C 0.82674(8) 0.0715(2) 0.59914(6) 0.0242(2) Uani 1 1 d . . . . .
H16 H 0.890292 0.122178 0.603651 0.029 Uiso 1 1 calc R U . . .
B1 B 0.76103(8) 0.5256(3) 0.74029(7) 0.0201(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.3492(11) . ?
F2 C4 1.3486(12) . ?
F3 C6 1.3419(13) . ?
O1 B1 1.3707(14) . ?
O1 C7 1.3819(13) . ?
O2 B1 1.3688(14) . ?
O2 C9 1.3879(12) . ?
C1 C2 1.3987(15) . ?
C1 C6 1.4004(14) . ?
C1 B1 1.5729(16) . ?
C2 C3 1.3820(15) . ?
C3 C4 1.3805(15) . ?
C3 H3 0.95 . ?
C4 C5 1.3735(16) . ?
C5 C6 1.3833(15) . ?
C5 H5 0.95 . ?
C7 C16 1.3646(16) . ?
C7 C8 1.4154(14) . ?
C8 C9 1.4105(15) . ?
C8 C13 1.4240(15) . ?
C9 C10 1.3657(15) . ?
C10 C11 1.4157(15) . ?
C10 H10 0.95 . ?
C11 C12 1.3686(17) . ?
C11 H11 0.95 . ?
C12 C13 1.4189(15) . ?
C12 H12 0.95 . ?
C13 C14 1.4191(16) . ?
C14 C15 1.3726(16) . ?
C14 H14 0.95 . ?
C15 C16 1.4150(16) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C7 120.20(9) . . ?
B1 O2 C9 119.81(9) . . ?
C2 C1 C6 113.07(9) . . ?
C2 C1 B1 123.92(9) . . ?
C6 C1 B1 123.01(10) . . ?
F1 C2 C3 115.77(9) . . ?
F1 C2 C1 118.89(9) . . ?
C3 C2 C1 125.34(10) . . ?
C4 C3 C2 116.41(10) . . ?
C4 C3 H3 121.8 . . ?
C2 C3 H3 121.8 . . ?
F2 C4 C5 118.26(10) . . ?
F2 C4 C3 118.37(10) . . ?
C5 C4 C3 123.36(10) . . ?
C4 C5 C6 116.52(10) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
F3 C6 C5 116.05(9) . . ?
F3 C6 C1 118.66(10) . . ?
C5 C6 C1 125.28(10) . . ?
C16 C7 O1 120.11(9) . . ?
C16 C7 C8 121.46(10) . . ?
O1 C7 C8 118.43(9) . . ?
C9 C8 C7 120.58(10) . . ?
C9 C8 C13 119.82(9) . . ?
C7 C8 C13 119.60(10) . . ?
C10 C9 O2 119.78(10) . . ?
C10 C9 C8 121.52(10) . . ?
O2 C9 C8 118.70(9) . . ?
C9 C10 C11 118.64(10) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 121.58(10) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.66(10) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 124.15(10) . . ?
C12 C13 C8 117.79(10) . . ?
C14 C13 C8 118.06(10) . . ?
C15 C14 C13 120.51(10) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.48(10) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C7 C16 C15 118.88(10) . . ?
C7 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
O2 B1 O1 122.27(10) . . ?
O2 B1 C1 119.43(10) . . ?
O1 B1 C1 118.30(9) . . ?

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1962510'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_date             2019-10-29T13:49:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H6 B F5 O2'
_chemical_formula_weight         336.02

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.30604(7)
_cell_length_b                   9.01092(6)
_cell_length_c                   15.64505(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.8492(7)
_cell_angle_gamma                90
_cell_volume                     1273.792(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15496
_cell_measurement_theta_min      4.863
_cell_measurement_theta_max      77.344

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.113
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 4 -4 0.1053
1 3 -9 0.1137
-2 0 -9 0.0848
-4 -3 -3 0.0937
0 -2 9 0.1079
-6 -1 4 0.0464
-4 4 4 0.1255
5 3 -3 0.0876
6 0 -4 0.0833
2 -5 -4 0.1164
5 1 2 0.0609
4 -4 4 0.1047
-2 -6 2 0.1283
-6 -1 -1 0.057
-5 2 -2 0.0781
0 6 -3 0.1099
6 1 1 0.0556
1 -3 8 0.1033
3 4 4 0.119
1 3 8 0.1126
-2 0 10 0.0836
2 0 -10 0.112
0 5 5 0.1284
-5 3 -2 0.0771
6 0 1 0.0555
-1 5 -5 0.1087
-5 0 -3 0.0599
4 0 -9 0.107
1 0 9 0.0889


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.854

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0435439
_diffrn_orient_matrix_ub_12      0.0181155
_diffrn_orient_matrix_ub_13      -0.1008424
_diffrn_orient_matrix_ub_21      -0.116494
_diffrn_orient_matrix_ub_22      0.1168871
_diffrn_orient_matrix_ub_23      0.0086969
_diffrn_orient_matrix_ub_31      0.1165964
_diffrn_orient_matrix_ub_32      0.123472
_diffrn_orient_matrix_ub_33      0.0065736
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_number            23436
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.894
_diffrn_reflns_theta_max         77.286
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_Friedel_coverage         0
_reflns_number_total             2676
_reflns_number_gt                2542
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.4823P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2676
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.076

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Inconsistent reflection 4 0 0 was omitted.
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 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'

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 0.80961(7) 0.53625(7) 0.43678(4) 0.01703(17) Uani 1 1 d . . . . .
F2 F 1.01329(7) 0.72993(8) 0.51429(5) 0.02002(18) Uani 1 1 d . . . . .
F3 F 1.05900(8) 0.78735(8) 0.68943(5) 0.02388(18) Uani 1 1 d . . . . .
F4 F 0.89733(8) 0.64240(8) 0.78679(4) 0.02259(18) Uani 1 1 d . . . . .
F5 F 0.69106(7) 0.44763(8) 0.71137(4) 0.01871(17) Uani 1 1 d . . . . .
O1 O 0.53287(8) 0.29634(9) 0.57266(5) 0.01434(18) Uani 1 1 d . . . . .
O2 O 0.60327(9) 0.33702(9) 0.43655(5) 0.01497(18) Uani 1 1 d . . . . .
C1 C 0.42779(12) 0.19209(12) 0.53269(7) 0.0131(2) Uani 1 1 d . . . . .
C2 C 0.41254(11) 0.16010(12) 0.44266(7) 0.0134(2) Uani 1 1 d . . . . .
C3 C 0.50114(12) 0.23303(12) 0.39384(7) 0.0137(2) Uani 1 1 d . . . . .
C4 C 0.48932(12) 0.20328(13) 0.30697(7) 0.0166(2) Uani 1 1 d . . . . .
H4 H 0.549477 0.253962 0.275185 0.02 Uiso 1 1 calc R U . . .
C5 C 0.38563(13) 0.09537(13) 0.26511(7) 0.0182(2) Uani 1 1 d . . . . .
H5 H 0.377382 0.072813 0.204813 0.022 Uiso 1 1 calc R U . . .
C6 C 0.29665(13) 0.02259(13) 0.31006(7) 0.0176(2) Uani 1 1 d . . . . .
H6 H 0.227496 -0.048974 0.280387 0.021 Uiso 1 1 calc R U . . .
C7 C 0.30694(12) 0.05318(12) 0.40030(7) 0.0148(2) Uani 1 1 d . . . . .
C8 C 0.21872(12) -0.01692(13) 0.45121(8) 0.0167(2) Uani 1 1 d . . . . .
H8 H 0.147041 -0.088618 0.424623 0.02 Uiso 1 1 calc R U . . .
C9 C 0.23630(12) 0.01822(13) 0.53868(8) 0.0168(2) Uani 1 1 d . . . . .
H9 H 0.176066 -0.02969 0.571524 0.02 Uiso 1 1 calc R U . . .
C10 C 0.34190(12) 0.12398(12) 0.58083(7) 0.0153(2) Uani 1 1 d . . . . .
H10 H 0.352979 0.147238 0.641286 0.018 Uiso 1 1 calc R U . . .
C11 C 0.73954(12) 0.47986(12) 0.57013(7) 0.0136(2) Uani 1 1 d . . . . .
C12 C 0.82612(12) 0.55790(12) 0.52345(7) 0.0142(2) Uani 1 1 d . . . . .
C13 C 0.93263(12) 0.66020(12) 0.56223(8) 0.0158(2) Uani 1 1 d . . . . .
C14 C 0.95633(12) 0.68876(13) 0.65113(8) 0.0170(2) Uani 1 1 d . . . . .
C15 C 0.87407(13) 0.61500(13) 0.70042(7) 0.0169(2) Uani 1 1 d . . . . .
C16 C 0.76780(12) 0.51354(12) 0.65972(7) 0.0148(2) Uani 1 1 d . . . . .
B1 B 0.61911(13) 0.36334(13) 0.52427(8) 0.0133(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C12 1.3418(12) . ?
F2 C13 1.3381(13) . ?
F3 C14 1.3368(13) . ?
F4 C15 1.3392(13) . ?
F5 C16 1.3385(13) . ?
O1 B1 1.3684(15) . ?
O1 C1 1.3917(13) . ?
O2 B1 1.3655(14) . ?
O2 C3 1.3870(13) . ?
C1 C10 1.3678(15) . ?
C1 C2 1.4112(15) . ?
C2 C3 1.4130(15) . ?
C2 C7 1.4218(15) . ?
C3 C4 1.3637(16) . ?
C4 C5 1.4152(16) . ?
C4 H4 0.95 . ?
C5 C6 1.3744(17) . ?
C5 H5 0.95 . ?
C6 C7 1.4191(15) . ?
C6 H6 0.95 . ?
C7 C8 1.4214(16) . ?
C8 C9 1.3757(16) . ?
C8 H8 0.95 . ?
C9 C10 1.4137(16) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C16 1.3962(15) . ?
C11 C12 1.3996(15) . ?
C11 B1 1.5775(16) . ?
C12 C13 1.3829(16) . ?
C13 C14 1.3792(16) . ?
C14 C15 1.3803(17) . ?
C15 C16 1.3849(16) . ?

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 C1 119.42(9) . . ?
B1 O2 C3 119.89(9) . . ?
C10 C1 O1 119.72(10) . . ?
C10 C1 C2 121.70(10) . . ?
O1 C1 C2 118.57(10) . . ?
C1 C2 C3 120.82(10) . . ?
C1 C2 C7 119.78(10) . . ?
C3 C2 C7 119.40(10) . . ?
C4 C3 O2 119.71(10) . . ?
C4 C3 C2 121.94(10) . . ?
O2 C3 C2 118.36(10) . . ?
C3 C4 C5 118.66(10) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.24(10) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.73(10) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 124.11(10) . . ?
C6 C7 C2 118.02(10) . . ?
C8 C7 C2 117.87(10) . . ?
C9 C8 C7 120.53(10) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.54(10) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C9 118.57(10) . . ?
C1 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C16 C11 C12 114.90(10) . . ?
C16 C11 B1 122.95(10) . . ?
C12 C11 B1 122.15(10) . . ?
F1 C12 C13 115.92(10) . . ?
F1 C12 C11 120.88(10) . . ?
C13 C12 C11 123.20(10) . . ?
F2 C13 C14 120.13(10) . . ?
F2 C13 C12 120.42(10) . . ?
C14 C13 C12 119.45(10) . . ?
F3 C14 C13 120.04(10) . . ?
F3 C14 C15 120.14(10) . . ?
C13 C14 C15 119.82(11) . . ?
F4 C15 C14 119.84(10) . . ?
F4 C15 C16 120.72(10) . . ?
C14 C15 C16 119.44(10) . . ?
F5 C16 C15 116.15(10) . . ?
F5 C16 C11 120.67(10) . . ?
C15 C16 C11 123.18(10) . . ?
O2 B1 O1 122.88(10) . . ?
O2 B1 C11 117.82(10) . . ?
O1 B1 C11 119.27(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_17a
_database_code_depnum_ccdc_archive 'CCDC 1962517'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_17a                 
;
PROBLEM: D-H Without Acceptor       N1       --H1       .     Please Check 
RESPONSE: The proton is orientated at a neighboring phenyl ring.
;
# end Validation Reply Form

_audit_creation_date             2019-06-20T09:48:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C76 H84 B6 N8 O12'
_chemical_formula_weight         1366.37

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R -3 :H'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_Int_Tables_number      148
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   16.70350(10)
_cell_length_b                   16.70350(10)
_cell_length_c                   23.0950(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5580.38(8)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12964
_cell_measurement_theta_min      3.585
_cell_measurement_theta_max      77.284

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.128
_exptl_crystal_density_diffrn    1.22
_exptl_crystal_F_000             2166
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 -1 0.1124
-8 9 7 0.097
2 8 -6 0.1215
-2 -8 6 0.1089
-8 0 -9 0.064
8 0 9 0.064
2 -10 6 0.1215
-2 9 -5 0.1307
0 8 -8 0.12


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.116
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.83
_shelx_estimated_absorpt_T_max   0.921

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0818136
_diffrn_orient_matrix_ub_12      -0.018527
_diffrn_orient_matrix_ub_13      -0.0395214
_diffrn_orient_matrix_ub_21      0.0475814
_diffrn_orient_matrix_ub_22      -0.0186498
_diffrn_orient_matrix_ub_23      -0.0511997
_diffrn_orient_matrix_ub_31      -0.0488254
_diffrn_orient_matrix_ub_32      -0.103178
_diffrn_orient_matrix_ub_33      0.0163271
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_number            15221
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.605
_diffrn_reflns_theta_max         77.45
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             2608
_reflns_number_gt                2491
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²+4.9089P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2608
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.000  0.000  0.500       128        24 ' '
   2  0.333  0.666  0.167       129        24 ' '
   3  0.667  0.333  0.833       129        24 ' '
_platon_squeeze_void_probe_radius                  1.20
_platon_squeeze_details                           ?

  The unit cell contains 3 interstitial disordered acetonitrile molecules 
  which have been treated as a diffuse contribution to the overall 
  scattering without specific atoms positions by PLATON/SQUEEZE. The 
  squeezed atoms were not included in the CIF due to uncertainty about
  the actual chemical identity of the molecule(s) in the void space.
  
  References:
  Spek, A.L. (2009). Acta Cryst. D65, 148-155.
  Spek, A.L. (2015). Acta Cryst. C71, 9-18.,SQUEEZE
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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 0.71709(5) 0.76160(5) 0.29546(3) 0.02456(19) Uani 1 1 d . . . . .
O2 O 0.70296(6) 0.78343(5) 0.39946(3) 0.0263(2) Uani 1 1 d . . . . .
N1 N 0.56185(7) 0.68935(6) 0.34151(4) 0.0278(2) Uani 1 1 d . . . . .
H1 H 0.570952 0.634818 0.345577 0.033 Uiso 1 1 calc R U . . .
C1 C 0.74998(7) 0.70425(7) 0.30786(4) 0.0202(2) Uani 1 1 d . . . . .
C2 C 0.75657(6) 0.68227(7) 0.36656(4) 0.0197(2) Uani 1 1 d . . . . .
C3 C 0.73107(7) 0.72230(7) 0.41220(5) 0.0222(2) Uani 1 1 d . . . . .
C4 C 0.73698(8) 0.70060(8) 0.46884(5) 0.0275(2) Uani 1 1 d . . . . .
H4 H 0.719067 0.726834 0.499147 0.033 Uiso 1 1 calc R U . . .
C5 C 0.76959(8) 0.63943(8) 0.48206(5) 0.0289(3) Uani 1 1 d . . . . .
H5 H 0.773643 0.624992 0.521357 0.035 Uiso 1 1 calc R U . . .
C6 C 0.79557(7) 0.60047(7) 0.43896(5) 0.0256(2) Uani 1 1 d . . . . .
H6 H 0.81745 0.559504 0.448687 0.031 Uiso 1 1 calc R U . . .
C7 C 0.78996(6) 0.62094(7) 0.38007(4) 0.0209(2) Uani 1 1 d . . . . .
C8 C 0.81639(7) 0.58344(7) 0.33353(5) 0.0222(2) Uani 1 1 d . . . . .
H8 H 0.837801 0.541477 0.341348 0.027 Uiso 1 1 calc R U . . .
C9 C 0.81123(7) 0.60738(7) 0.27727(5) 0.0232(2) Uani 1 1 d . . . . .
H9 H 0.830486 0.582608 0.246817 0.028 Uiso 1 1 calc R U . . .
C10 C 0.77798(7) 0.66792(7) 0.26375(4) 0.0224(2) Uani 1 1 d . . . . .
H10 H 0.774868 0.683592 0.224596 0.027 Uiso 1 1 calc R U . . .
C11 C 0.51025(9) 0.67545(9) 0.28676(6) 0.0400(3) Uani 1 1 d . . . . .
H11A H 0.548986 0.678493 0.254012 0.06 Uiso 1 1 calc R U . . .
H11B H 0.493828 0.723879 0.282703 0.06 Uiso 1 1 calc R U . . .
H11C H 0.453819 0.614784 0.287365 0.06 Uiso 1 1 calc R U . . .
C12 C 0.50464(10) 0.68592(9) 0.39184(6) 0.0407(3) Uani 1 1 d . . . . .
H12A H 0.496716 0.740211 0.391158 0.061 Uiso 1 1 calc R U . . .
H12B H 0.535552 0.68563 0.427839 0.061 Uiso 1 1 calc R U . . .
H12C H 0.443975 0.629646 0.389667 0.061 Uiso 1 1 calc R U . . .
B1 B 0.66808(8) 0.78308(8) 0.34096(5) 0.0235(2) Uani 1 1 d . . . . .
N2 N 0.333333 0.666667 0.47822(10) 0.0642(7) Uani 1 3 d S T P . .
C13 C 0.333333 0.666667 0.52748(10) 0.0388(5) Uani 1 3 d S T P . .
C14 C 0.333333 0.666667 0.59041(9) 0.0359(5) Uani 1 3 d S T P . .
H14A H 0.276277 0.663001 0.604559 0.054 Uiso 0.3333 1 calc R U P . .
H14B H 0.386724 0.723724 0.604559 0.054 Uiso 0.3333 1 calc R U P . .
H14C H 0.336999 0.613276 0.604559 0.054 Uiso 0.3333 1 calc R U P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 1.3519(12) . ?
O1 B1 1.4821(13) . ?
O2 C3 1.3523(12) . ?
O2 B1 1.4704(14) . ?
N1 C11 1.4816(16) . ?
N1 C12 1.4874(15) . ?
N1 B1 1.6799(16) . ?
N1 H1 1 . ?
C1 C10 1.3816(14) . ?
C1 C2 1.4229(14) . ?
C2 C3 1.4228(14) . ?
C2 C7 1.4246(14) . ?
C3 C4 1.3740(15) . ?
C4 C5 1.4111(16) . ?
C4 H4 0.95 . ?
C5 C6 1.3729(16) . ?
C5 H5 0.95 . ?
C6 C7 1.4167(14) . ?
C6 H6 0.95 . ?
C7 C8 1.4211(14) . ?
C8 C9 1.3747(15) . ?
C8 H8 0.95 . ?
C9 C10 1.4106(14) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
B1 B1 1.739(2) 16_665 ?
N2 C13 1.138(3) . ?
C13 C14 1.453(3) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?

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 119.39(8) . . ?
C3 O2 B1 118.91(8) . . ?
C11 N1 C12 110.40(10) . . ?
C11 N1 B1 113.58(9) . . ?
C12 N1 B1 113.62(9) . . ?
C11 N1 H1 106.2 . . ?
C12 N1 H1 106.2 . . ?
B1 N1 H1 106.2 . . ?
O1 C1 C10 120.12(9) . . ?
O1 C1 C2 119.73(9) . . ?
C10 C1 C2 120.16(9) . . ?
C3 C2 C1 120.31(9) . . ?
C3 C2 C7 119.50(9) . . ?
C1 C2 C7 120.19(9) . . ?
O2 C3 C4 120.27(9) . . ?
O2 C3 C2 119.48(9) . . ?
C4 C3 C2 120.23(9) . . ?
C3 C4 C5 120.12(10) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.94(10) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.46(10) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 123.17(9) . . ?
C6 C7 C2 118.74(9) . . ?
C8 C7 C2 118.09(9) . . ?
C9 C8 C7 120.54(9) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.48(9) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C1 C10 C9 119.51(9) . . ?
C1 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 B1 O1 112.74(9) . . ?
O2 B1 N1 103.21(8) . . ?
O1 B1 N1 103.51(8) . . ?
O2 B1 B1 112.61(11) . 16_665 ?
O1 B1 B1 112.03(11) . 16_665 ?
N1 B1 B1 112.05(11) . 16_665 ?
N2 C13 C14 180 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?


####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1962511'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_3a                  
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.469 Check 
RESPONSE: The crystals were poor diffractors at high anlges.
;
_vrf_PLAT911_3a                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: These reflections were not collected using omega only scans.
;
# end Validation Reply Form

_audit_creation_date             2018-05-28T11:37:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H8 B F3 O2'
_chemical_formula_weight         300.03

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.000(2)
_cell_length_b                   9.222(2)
_cell_length_c                   15.177(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.643(3)
_cell_angle_gamma                90
_cell_volume                     1229.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1528
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.26

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       blade
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             608

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5830
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.996

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_number            7797
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         25.444
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             2270
_reflns_number_gt                1588
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+0.2792P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2270
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.096
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.89775(15) 0.63385(14) 0.78837(8) 0.0263(4) Uani 1 1 d . . . . .
F2 F 1.05881(14) 0.78237(14) 0.68842(9) 0.0261(4) Uani 1 1 d . . . . .
F3 F 1.01378(14) 0.73461(13) 0.50906(9) 0.0226(3) Uani 1 1 d . . . . .
O1 O 0.53619(16) 0.29383(15) 0.56959(9) 0.0157(4) Uani 1 1 d . . . . .
O2 O 0.61517(16) 0.33486(15) 0.43024(10) 0.0164(4) Uani 1 1 d . . . . .
C1 C 0.4299(2) 0.1906(2) 0.52847(14) 0.0144(5) Uani 1 1 d . . . . .
C2 C 0.4188(2) 0.1609(2) 0.43591(14) 0.0150(5) Uani 1 1 d . . . . .
C3 C 0.5122(2) 0.2312(2) 0.38642(15) 0.0149(5) Uani 1 1 d . . . . .
C4 C 0.5062(3) 0.2007(2) 0.29802(15) 0.0178(5) Uani 1 1 d . . . . .
H4 H 0.571472 0.248804 0.266002 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4007(2) 0.0957(2) 0.25499(15) 0.0188(5) Uani 1 1 d . . . . .
H5 H 0.395352 0.072743 0.193355 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3056(2) 0.0262(2) 0.30069(15) 0.0182(5) Uani 1 1 d . . . . .
H6 H 0.23464 -0.042929 0.269947 0.022 Uiso 1 1 calc R U . . .
C7 C 0.3117(2) 0.0559(2) 0.39264(15) 0.0153(5) Uani 1 1 d . . . . .
C8 C 0.2189(2) -0.0123(2) 0.44450(15) 0.0182(5) Uani 1 1 d . . . . .
H8 H 0.145614 -0.081973 0.416881 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2330(2) 0.0207(2) 0.53395(15) 0.0169(5) Uani 1 1 d . . . . .
H9 H 0.169708 -0.026947 0.567434 0.02 Uiso 1 1 calc R U . . .
C10 C 0.3394(2) 0.1236(2) 0.57703(15) 0.0158(5) Uani 1 1 d . . . . .
H10 H 0.348003 0.146032 0.639036 0.019 Uiso 1 1 calc R U . . .
C11 C 0.7421(2) 0.4785(2) 0.56696(15) 0.0153(5) Uani 1 1 d . . . . .
C12 C 0.7669(2) 0.5053(2) 0.65965(15) 0.0171(5) Uani 1 1 d . . . . .
H12 H 0.710865 0.453074 0.695506 0.02 Uiso 1 1 calc R U . . .
C13 C 0.8720(2) 0.6068(2) 0.69892(15) 0.0184(5) Uani 1 1 d . . . . .
C14 C 0.9552(2) 0.6839(2) 0.64872(15) 0.0181(5) Uani 1 1 d . . . . .
C15 C 0.9310(2) 0.6581(2) 0.55698(15) 0.0159(5) Uani 1 1 d . . . . .
C16 C 0.8265(2) 0.5575(2) 0.51591(15) 0.0168(5) Uani 1 1 d . . . . .
H16 H 0.811263 0.541255 0.452755 0.02 Uiso 1 1 calc R U . . .
B1 B 0.6257(3) 0.3622(3) 0.52001(17) 0.0157(6) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.350(2) . ?
F2 C14 1.345(2) . ?
F3 C15 1.349(2) . ?
O1 B1 1.371(3) . ?
O1 C1 1.396(2) . ?
O2 B1 1.368(3) . ?
O2 C3 1.394(2) . ?
C1 C10 1.361(3) . ?
C1 C2 1.413(3) . ?
C2 C3 1.403(3) . ?
C2 C7 1.422(3) . ?
C3 C4 1.360(3) . ?
C4 C5 1.413(3) . ?
C4 H4 0.95 . ?
C5 C6 1.372(3) . ?
C5 H5 0.95 . ?
C6 C7 1.412(3) . ?
C6 H6 0.95 . ?
C7 C8 1.415(3) . ?
C8 C9 1.370(3) . ?
C8 H8 0.95 . ?
C9 C10 1.404(3) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.397(3) . ?
C11 C16 1.402(3) . ?
C11 B1 1.558(3) . ?
C12 C13 1.371(3) . ?
C12 H12 0.95 . ?
C13 C14 1.378(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.370(3) . ?
C16 H16 0.95 . ?

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 C1 119.72(17) . . ?
B1 O2 C3 119.69(17) . . ?
C10 C1 O1 120.02(19) . . ?
C10 C1 C2 122.0(2) . . ?
O1 C1 C2 117.97(18) . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 C7 119.5(2) . . ?
C1 C2 C7 118.98(19) . . ?
C4 C3 O2 119.41(19) . . ?
C4 C3 C2 122.2(2) . . ?
O2 C3 C2 118.35(19) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 124.4(2) . . ?
C6 C7 C2 117.7(2) . . ?
C8 C7 C2 118.0(2) . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C1 C10 C9 118.9(2) . . ?
C1 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C16 118.5(2) . . ?
C12 C11 B1 121.7(2) . . ?
C16 C11 B1 119.7(2) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
F1 C13 C12 120.9(2) . . ?
F1 C13 C14 117.8(2) . . ?
C12 C13 C14 121.3(2) . . ?
F2 C14 C13 120.5(2) . . ?
F2 C14 C15 120.56(19) . . ?
C13 C14 C15 118.9(2) . . ?
F3 C15 C16 120.9(2) . . ?
F3 C15 C14 117.99(19) . . ?
C16 C15 C14 121.1(2) . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O2 B1 O1 122.7(2) . . ?
O2 B1 C11 118.4(2) . . ?
O1 B1 C11 118.9(2) . . ?

####################################################################### 
# 
# 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_18a
_database_code_depnum_ccdc_archive 'CCDC 1962518'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT094_18a                 
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.06 Report
RESPONSE: Due to very slight disorder of the ethyl groups about the P1 atom 
          that was not modeled.
;
_vrf_PLAT906_18a                 
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.196 Check 
RESPONSE: Due to weak high angle data.
;
# end Validation Reply Form

_audit_creation_date             2019-08-13T08:54:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H36 B Cl O4 P2'
_chemical_formula_weight         472.71

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.88720(10)
_cell_length_b                   19.09820(10)
_cell_length_c                   11.32260(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.3290(10)
_cell_angle_gamma                90
_cell_volume                     2511.22(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    26797
_cell_measurement_theta_min      3.784
_cell_measurement_theta_max      76.879

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.026
_exptl_crystal_density_diffrn    1.25
_exptl_crystal_F_000             1008
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 12 0 0.0176
-1 -12 0 0.0135
0 -10 -4 0.0553
-1 8 6 0.0754
-7 0 0 0.0168
7 0 0 0.0093
1 10 -4 0.0617
8 2 -1 0.0213
3 11 0 0.0161
-2 12 -1 0.0176
-5 9 -1 0.0199
-5 -4 -4 0.0617
6 -7 -4 0.0547


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.749
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.161
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.582
_shelx_estimated_absorpt_T_max   0.932

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.132533
_diffrn_orient_matrix_ub_12      0.0033425
_diffrn_orient_matrix_ub_13      -0.0306662
_diffrn_orient_matrix_ub_21      0.0020944
_diffrn_orient_matrix_ub_22      0.0429555
_diffrn_orient_matrix_ub_23      0.1156054
_diffrn_orient_matrix_ub_31      0.0051071
_diffrn_orient_matrix_ub_32      0.0682034
_diffrn_orient_matrix_ub_33      -0.0713447
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_number            47551
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.806
_diffrn_reflns_theta_max         77.333
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.981
_reflns_Friedel_coverage         0
_reflns_number_total             5232
_reflns_number_gt                4853
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+1.5738P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5232
_refine_ls_number_parameters     330
_refine_ls_number_restraints     113
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The ethyl groups bound to P2 (C17 < C22) were positionally disordered over 
 two sites (A and B). The sites occupancies for the A and B sites were 0.93
 and 0.07, respectively.  To help maintain reasonable ADP values and atom 
 positions for the minor components, SIMU, DELU, DFIX and EADP restraints and
 constraints were applied where needed. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.71630(3) 0.69912(2) 0.74768(3) 0.02414(11) Uani 1 1 d . . . . .
P1 P 0.74275(3) 0.61179(2) 0.44528(3) 0.02060(11) Uani 1 1 d . . . . .
P2 P 0.69740(3) 0.57947(2) 0.02420(3) 0.02100(11) Uani 1 1 d . . . . .
O1 O 0.66740(10) 0.47240(6) 0.30863(10) 0.0222(2) Uani 1 1 d . . . . .
O2 O 0.85287(10) 0.49000(6) 0.25252(10) 0.0228(2) Uani 1 1 d . . . . .
O3 O 0.75614(11) 0.58471(6) 0.31989(10) 0.0265(3) Uani 1 1 d . . . . .
O4 O 0.67623(10) 0.53200(6) 0.12803(10) 0.0237(2) Uani 1 1 d . . . . .
C1 C 0.67398(14) 0.40216(8) 0.28917(13) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.77059(13) 0.37511(9) 0.24893(13) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.85947(14) 0.42025(9) 0.22897(14) 0.0217(3) Uani 1 1 d . . . . .
C4 C 0.95397(15) 0.39403(10) 0.19178(15) 0.0277(4) Uani 1 1 d . . . . .
H4 H 1.01289 0.424606 0.178018 0.033 Uiso 1 1 calc R U . . .
C5 C 0.96248(16) 0.32121(10) 0.17426(17) 0.0327(4) Uani 1 1 d . . . . .
H5 H 1.02801 0.303 0.149207 0.039 Uiso 1 1 calc R U . . .
C6 C 0.87810(17) 0.27634(10) 0.19269(18) 0.0333(4) Uani 1 1 d . . . . .
H6 H 0.885658 0.227568 0.179781 0.04 Uiso 1 1 calc R U . . .
C7 C 0.77946(15) 0.30179(9) 0.23086(16) 0.0273(4) Uani 1 1 d . . . . .
C8 C 0.69032(17) 0.25784(10) 0.25318(18) 0.0335(4) Uani 1 1 d . . . . .
H8 H 0.694866 0.208683 0.242219 0.04 Uiso 1 1 calc R U . . .
C9 C 0.59743(16) 0.28580(10) 0.29053(17) 0.0321(4) Uani 1 1 d . . . . .
H9 H 0.537874 0.255648 0.304029 0.038 Uiso 1 1 calc R U . . .
C10 C 0.58862(14) 0.35841(9) 0.30929(15) 0.0255(3) Uani 1 1 d . . . . .
H10 H 0.523954 0.376872 0.335677 0.031 Uiso 1 1 calc R U . . .
C11 C 0.84730(15) 0.67915(9) 0.48913(15) 0.0245(3) Uani 1 1 d . . . . .
H11A H 0.826642 0.719117 0.433005 0.029 Uiso 1 1 calc R U . . .
H11B H 0.842664 0.695616 0.570865 0.029 Uiso 1 1 calc R U . . .
C12 C 0.97189(15) 0.65860(10) 0.49119(16) 0.0291(4) Uani 1 1 d . . . . .
H12A H 0.977325 0.639741 0.412105 0.044 Uiso 1 1 calc R U . . .
H12B H 0.996874 0.622933 0.553495 0.044 Uiso 1 1 calc R U . . .
H12C H 1.021415 0.699942 0.509287 0.044 Uiso 1 1 calc R U . . .
C13 C 0.60424(15) 0.65173(9) 0.43182(15) 0.0254(3) Uani 1 1 d . . . . .
H13A H 0.600384 0.673455 0.510238 0.031 Uiso 1 1 calc R U . . .
H13B H 0.596285 0.689622 0.370932 0.031 Uiso 1 1 calc R U . . .
C14 C 0.50288(16) 0.60145(11) 0.39554(17) 0.0333(4) Uani 1 1 d . . . . .
H14A H 0.430524 0.627616 0.385348 0.05 Uiso 1 1 calc R U . . .
H14B H 0.50598 0.566017 0.458759 0.05 Uiso 1 1 calc R U . . .
H14C H 0.50707 0.578447 0.319231 0.05 Uiso 1 1 calc R U . . .
C15 C 0.75503(15) 0.54389(9) 0.55784(14) 0.0253(3) Uani 1 1 d . . . . .
H15A H 0.75898 0.566499 0.637295 0.03 Uiso 1 1 calc R U . . .
H15B H 0.683556 0.51566 0.539818 0.03 Uiso 1 1 calc R U . . .
C16 C 0.85714(16) 0.49401(9) 0.56970(16) 0.0285(4) Uani 1 1 d . . . . .
H16A H 0.856901 0.47253 0.491046 0.043 Uiso 1 1 calc R U . . .
H16B H 0.851132 0.457373 0.628635 0.043 Uiso 1 1 calc R U . . .
H16C H 0.928972 0.520111 0.597046 0.043 Uiso 1 1 calc R U . . .
C17A C 0.64993(16) 0.53098(10) -0.11393(16) 0.0255(4) Uani 0.927(3) 1 d D U P A
1
H17A H 0.570067 0.514674 -0.118466 0.031 Uiso 0.927(3) 1 calc R U P A 1
H17B H 0.649289 0.562499 -0.183494 0.031 Uiso 0.927(3) 1 calc R U P A 1
C18A C 0.7265(2) 0.46769(12) -0.1238(2) 0.0316(5) Uani 0.927(3) 1 d D . P A 1
H18A H 0.691272 0.43973 -0.194617 0.047 Uiso 0.927(3) 1 calc R U P A 1
H18B H 0.734515 0.438953 -0.050729 0.047 Uiso 0.927(3) 1 calc R U P A 1
H18C H 0.802568 0.483878 -0.132236 0.047 Uiso 0.927(3) 1 calc R U P A 1
C19A C 0.84402(16) 0.60293(10) 0.02902(16) 0.0273(4) Uani 0.927(3) 1 d D U P A
1
H19A H 0.888443 0.559186 0.027743 0.033 Uiso 0.927(3) 1 calc R U P A 1
H19B H 0.846586 0.628883 -0.04604 0.033 Uiso 0.927(3) 1 calc R U P A 1
C20A C 0.9062(2) 0.64713(19) 0.1365(3) 0.0298(7) Uani 0.927(3) 1 d D U P A 1
H20A H 0.977257 0.66635 0.118771 0.045 Uiso 0.927(3) 1 calc R U P A 1
H20B H 0.925121 0.617683 0.208961 0.045 Uiso 0.927(3) 1 calc R U P A 1
H20C H 0.856058 0.685578 0.15053 0.045 Uiso 0.927(3) 1 calc R U P A 1
C21A C 0.61175(17) 0.65742(10) 0.01751(16) 0.0259(4) Uani 0.927(3) 1 d D U P A
1
H21A H 0.64581 0.688222 0.086183 0.031 Uiso 0.927(3) 1 calc R U P A 1
H21B H 0.613737 0.682928 -0.058139 0.031 Uiso 0.927(3) 1 calc R U P A 1
C22A C 0.4863(2) 0.64200(16) 0.0219(3) 0.0302(6) Uani 0.927(3) 1 d D U P A 1
H22A H 0.440935 0.685103 0.005712 0.045 Uiso 0.927(3) 1 calc R U P A 1
H22B H 0.48269 0.624221 0.102234 0.045 Uiso 0.927(3) 1 calc R U P A 1
H22C H 0.455099 0.606795 -0.039274 0.045 Uiso 0.927(3) 1 calc R U P A 1
C17B C 0.788(2) 0.5219(12) -0.053(2) 0.028(3) Uani 0.073(3) 1 d D U P A 2
H17C H 0.80218 0.546249 -0.125253 0.034 Uiso 0.073(3) 1 calc R U P A 2
H17D H 0.863412 0.514059 0.00283 0.034 Uiso 0.073(3) 1 calc R U P A 2
C18B C 0.731(4) 0.4502(15) -0.091(3) 0.0316(5) Uani 0.073(3) 1 d D U P A 2
H18D H 0.787444 0.418403 -0.11305 0.047 Uiso 0.073(3) 1 calc R U P A 2
H18E H 0.666313 0.4566 -0.159975 0.047 Uiso 0.073(3) 1 calc R U P A 2
H18F H 0.702103 0.430115 -0.022979 0.047 Uiso 0.073(3) 1 calc R U P A 2
C19B C 0.793(2) 0.6510(13) 0.0725(19) 0.028(4) Uani 0.073(3) 1 d D U P A 2
H19C H 0.782553 0.685076 0.005098 0.034 Uiso 0.073(3) 1 calc R U P A 2
H19D H 0.767294 0.674371 0.140131 0.034 Uiso 0.073(3) 1 calc R U P A 2
C20B C 0.924(3) 0.637(3) 0.114(4) 0.032(6) Uani 0.073(3) 1 d D U P A 2
H20D H 0.965902 0.681848 0.11674 0.049 Uiso 0.073(3) 1 calc R U P A 2
H20E H 0.949442 0.605577 0.057002 0.049 Uiso 0.073(3) 1 calc R U P A 2
H20F H 0.940058 0.616231 0.19476 0.049 Uiso 0.073(3) 1 calc R U P A 2
C21B C 0.574(2) 0.5972(13) -0.063(2) 0.028(3) Uani 0.073(3) 1 d D U P A 2
H21C H 0.583438 0.620297 -0.13907 0.033 Uiso 0.073(3) 1 calc R U P A 2
H21D H 0.526136 0.554718 -0.083265 0.033 Uiso 0.073(3) 1 calc R U P A 2
C22B C 0.525(3) 0.6472(19) 0.018(4) 0.029(5) Uani 0.073(3) 1 d D U P A 2
H22D H 0.441301 0.649601 -0.008849 0.044 Uiso 0.073(3) 1 calc R U P A 2
H22E H 0.558228 0.693912 0.014497 0.044 Uiso 0.073(3) 1 calc R U P A 2
H22F H 0.544614 0.63002 0.10182 0.044 Uiso 0.073(3) 1 calc R U P A 2
B1 B 0.74001(16) 0.51755(10) 0.25487(16) 0.0209(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
P1 O3 1.5507(11) . ?
P1 C11 1.7840(17) . ?
P1 C13 1.7914(18) . ?
P1 C15 1.8022(17) . ?
P2 O4 1.5473(11) . ?
P2 C21B 1.62(2) . ?
P2 C19B 1.79(2) . ?
P2 C19A 1.7890(19) . ?
P2 C21A 1.7960(19) . ?
P2 C17A 1.8015(18) . ?
P2 C17B 1.88(2) . ?
O1 C1 1.3645(19) . ?
O1 B1 1.443(2) . ?
O2 C3 1.364(2) . ?
O2 B1 1.447(2) . ?
O3 B1 1.471(2) . ?
O4 B1 1.499(2) . ?
C1 C10 1.371(2) . ?
C1 C2 1.420(2) . ?
C2 C3 1.419(2) . ?
C2 C7 1.422(2) . ?
C3 C4 1.376(2) . ?
C4 C5 1.411(3) . ?
C4 H4 0.95 . ?
C5 C6 1.369(3) . ?
C5 H5 0.95 . ?
C6 C7 1.419(2) . ?
C6 H6 0.95 . ?
C7 C8 1.416(3) . ?
C8 C9 1.372(3) . ?
C8 H8 0.95 . ?
C9 C10 1.410(3) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.528(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C14 1.527(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C16 1.526(2) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17A C18A 1.531(3) . ?
C17A H17A 0.99 . ?
C17A H17B 0.99 . ?
C18A H18A 0.98 . ?
C18A H18B 0.98 . ?
C18A H18C 0.98 . ?
C19A C20A 1.535(3) . ?
C19A H19A 0.99 . ?
C19A H19B 0.99 . ?
C20A H20A 0.98 . ?
C20A H20B 0.98 . ?
C20A H20C 0.98 . ?
C21A C22A 1.531(3) . ?
C21A H21A 0.99 . ?
C21A H21B 0.99 . ?
C22A H22A 0.98 . ?
C22A H22B 0.98 . ?
C22A H22C 0.98 . ?
C17B C18B 1.55(2) . ?
C17B H17C 0.99 . ?
C17B H17D 0.99 . ?
C18B H18D 0.98 . ?
C18B H18E 0.98 . ?
C18B H18F 0.98 . ?
C19B C20B 1.55(2) . ?
C19B H19C 0.99 . ?
C19B H19D 0.99 . ?
C20B H20D 0.98 . ?
C20B H20E 0.98 . ?
C20B H20F 0.98 . ?
C21B C22B 1.53(2) . ?
C21B H21C 0.99 . ?
C21B H21D 0.99 . ?
C22B H22D 0.98 . ?
C22B H22E 0.98 . ?
C22B H22F 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 P1 C11 107.08(7) . . ?
O3 P1 C13 109.65(7) . . ?
C11 P1 C13 106.84(8) . . ?
O3 P1 C15 113.51(7) . . ?
C11 P1 C15 112.06(8) . . ?
C13 P1 C15 107.50(8) . . ?
O4 P2 C21B 108.4(8) . . ?
O4 P2 C19B 114.3(7) . . ?
C21B P2 C19B 117.5(12) . . ?
O4 P2 C19A 116.04(8) . . ?
O4 P2 C21A 109.57(8) . . ?
C19A P2 C21A 109.49(9) . . ?
O4 P2 C17A 106.66(8) . . ?
C19A P2 C17A 106.13(9) . . ?
C21A P2 C17A 108.65(9) . . ?
O4 P2 C17B 102.2(7) . . ?
C21B P2 C17B 111.8(11) . . ?
C19B P2 C17B 101.5(10) . . ?
C1 O1 B1 117.33(12) . . ?
C3 O2 B1 116.81(13) . . ?
B1 O3 P1 136.14(10) . . ?
B1 O4 P2 134.79(11) . . ?
O1 C1 C10 120.17(15) . . ?
O1 C1 C2 119.18(14) . . ?
C10 C1 C2 120.65(15) . . ?
C3 C2 C1 120.72(15) . . ?
C3 C2 C7 119.66(15) . . ?
C1 C2 C7 119.61(15) . . ?
O2 C3 C4 120.02(15) . . ?
O2 C3 C2 119.11(14) . . ?
C4 C3 C2 120.81(15) . . ?
C3 C4 C5 119.31(16) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 121.24(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.80(17) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 123.34(17) . . ?
C8 C7 C2 118.47(16) . . ?
C6 C7 C2 118.19(16) . . ?
C9 C8 C7 120.42(17) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.32(17) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C1 C10 C9 119.54(16) . . ?
C1 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 P1 115.75(12) . . ?
C12 C11 H11A 108.3 . . ?
P1 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
P1 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 P1 114.41(12) . . ?
C14 C13 H13A 108.7 . . ?
P1 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
P1 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 P1 117.01(12) . . ?
C16 C15 H15A 108 . . ?
P1 C15 H15A 108 . . ?
C16 C15 H15B 108 . . ?
P1 C15 H15B 108 . . ?
H15A C15 H15B 107.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18A C17A P2 112.84(14) . . ?
C18A C17A H17A 109 . . ?
P2 C17A H17A 109 . . ?
C18A C17A H17B 109 . . ?
P2 C17A H17B 109 . . ?
H17A C17A H17B 107.8 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C20A C19A P2 117.59(16) . . ?
C20A C19A H19A 107.9 . . ?
P2 C19A H19A 107.9 . . ?
C20A C19A H19B 107.9 . . ?
P2 C19A H19B 107.9 . . ?
H19A C19A H19B 107.2 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C22A C21A P2 112.73(15) . . ?
C22A C21A H21A 109 . . ?
P2 C21A H21A 109 . . ?
C22A C21A H21B 109 . . ?
P2 C21A H21B 109 . . ?
H21A C21A H21B 107.8 . . ?
C21A C22A H22A 109.5 . . ?
C21A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C21A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C18B C17B P2 113(2) . . ?
C18B C17B H17C 109.1 . . ?
P2 C17B H17C 109.1 . . ?
C18B C17B H17D 109.1 . . ?
P2 C17B H17D 109.1 . . ?
H17C C17B H17D 107.8 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C20B C19B P2 120(3) . . ?
C20B C19B H19C 107.4 . . ?
P2 C19B H19C 107.4 . . ?
C20B C19B H19D 107.4 . . ?
P2 C19B H19D 107.4 . . ?
H19C C19B H19D 106.9 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C22B C21B P2 100(2) . . ?
C22B C21B H21C 111.8 . . ?
P2 C21B H21C 111.8 . . ?
C22B C21B H21D 111.8 . . ?
P2 C21B H21D 111.8 . . ?
H21C C21B H21D 109.5 . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
O1 B1 O2 115.53(14) . . ?
O1 B1 O3 109.61(13) . . ?
O2 B1 O3 107.70(14) . . ?
O1 B1 O4 106.75(13) . . ?
O2 B1 O4 109.31(12) . . ?
O3 B1 O4 107.70(13) . . ?

####################################################################### 
# 
# 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_8a
_database_code_depnum_ccdc_archive 'CCDC 1962514'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT094_8a                  
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.13 Report
RESPONSE: The top 20 Q-peaks in the difference Fourier map were all located in 
          the bonds between C-C and C-B atoms.
;
# end Validation Reply Form

_audit_creation_date             2017-01-27T16:48:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H15 B O4'
_chemical_formula_weight         306.11

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7613(5)
_cell_length_b                   23.5453(15)
_cell_length_c                   8.1854(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.4110(10)
_cell_angle_gamma                90
_cell_volume                     1479.73(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9096
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.95

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       blocky
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             640

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6988
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.986

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_number            18004
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         27.954
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             3537
_reflns_number_gt                3184
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.5665P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3537
_refine_ls_number_parameters     210
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.63810(9) 0.35751(3) 0.50654(9) 0.01389(16) Uani 1 d . .
O2 O 0.84434(9) 0.43390(3) 0.52421(9) 0.01306(16) Uani 1 d . .
O3 O 0.97187(10) 0.28718(3) 0.61874(9) 0.01815(17) Uani 1 d . .
O4 O 0.84956(10) 0.40121(3) 0.15153(9) 0.01820(17) Uani 1 d . .
C1 C 0.53018(12) 0.38862(4) 0.59381(12) 0.0127(2) Uani 1 d . .
C2 C 0.37799(13) 0.36547(4) 0.62746(13) 0.0159(2) Uani 1 d . .
H2 H 0.3457 0.328 0.5929 0.019 Uiso 1 calc . .
C3 C 0.26934(13) 0.39838(5) 0.71477(13) 0.0179(2) Uani 1 d . .
H3 H 0.1627 0.3827 0.7378 0.021 Uiso 1 calc . .
C4 C 0.31454(13) 0.45239(5) 0.76692(13) 0.0165(2) Uani 1 d . .
H4 H 0.2391 0.4736 0.8253 0.02 Uiso 1 calc . .
C5 C 0.47332(13) 0.47691(4) 0.73432(12) 0.0136(2) Uani 1 d . .
C6 C 0.52986(13) 0.53238(4) 0.78481(12) 0.0155(2) Uani 1 d . .
H6 H 0.4602 0.5552 0.8451 0.019 Uiso 1 calc . .
C7 C 0.68449(13) 0.55322(4) 0.74707(13) 0.0157(2) Uani 1 d . .
H7 H 0.7195 0.5906 0.7812 0.019 Uiso 1 calc . .
C8 C 0.79292(13) 0.52063(4) 0.65875(12) 0.0141(2) Uani 1 d . .
H8 H 0.8999 0.5355 0.6341 0.017 Uiso 1 calc . .
C9 C 0.74008(12) 0.46716(4) 0.60963(12) 0.01160(19) Uani 1 d . .
C10 C 0.58158(12) 0.44414(4) 0.64515(11) 0.01137(19) Uani 1 d . .
C11 C 0.91174(12) 0.34225(4) 0.38070(12) 0.01268(19) Uani 1 d . .
C12 C 0.99294(13) 0.29403(4) 0.45646(13) 0.0146(2) Uani 1 d . .
C13 C 1.08878(14) 0.25704(4) 0.37136(14) 0.0195(2) Uani 1 d . .
H13 H 1.1426 0.2243 0.424 0.023 Uiso 1 calc . .
C14 C 1.10360(14) 0.26919(5) 0.20824(15) 0.0209(2) Uani 1 d . .
H14 H 1.1672 0.244 0.1489 0.025 Uiso 1 calc . .
C15 C 1.02825(14) 0.31712(5) 0.12927(13) 0.0180(2) Uani 1 d . .
H15 H 1.0413 0.3252 0.018 0.022 Uiso 1 calc . .
C16 C 0.93264(13) 0.35332(4) 0.21722(12) 0.0142(2) Uani 1 d . .
C17 C 1.05149(17) 0.23869(5) 0.70418(16) 0.0260(3) Uani 1 d . .
H17A H 1.009 0.204 0.6452 0.039 Uiso 1 calc . .
H17B H 1.0218 0.2377 0.8165 0.039 Uiso 1 calc . .
H17C H 1.1782 0.2411 0.7094 0.039 Uiso 1 calc . .
C18 C 0.87149(16) 0.41667(5) -0.01243(13) 0.0233(2) Uani 1 d . .
H18A H 0.8277 0.3861 -0.0886 0.035 Uiso 1 calc . .
H18B H 0.9954 0.4229 -0.0177 0.035 Uiso 1 calc . .
H18C H 0.8065 0.4516 -0.0438 0.035 Uiso 1 calc . .
B1 B 0.79245(14) 0.38036(5) 0.47459(13) 0.0121(2) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3729(13) . ?
O1 C1 1.3869(11) . ?
O2 B1 1.3667(13) . ?
O2 C9 1.3866(11) . ?
O3 C12 1.3714(13) . ?
O3 C17 1.4312(13) . ?
O4 C16 1.3693(12) . ?
O4 C18 1.4246(13) . ?
C1 C2 1.3650(14) . ?
C1 C10 1.4127(14) . ?
C2 C3 1.4137(14) . ?
C2 H2 0.95 . ?
C3 C4 1.3707(15) . ?
C3 H3 0.95 . ?
C4 C5 1.4211(14) . ?
C4 H4 0.95 . ?
C5 C10 1.4189(13) . ?
C5 C6 1.4199(14) . ?
C6 C7 1.3730(15) . ?
C6 H6 0.95 . ?
C7 C8 1.4136(14) . ?
C7 H7 0.95 . ?
C8 C9 1.3661(14) . ?
C8 H8 0.95 . ?
C9 C10 1.4129(13) . ?
C11 C16 1.3958(14) . ?
C11 C12 1.3988(14) . ?
C11 B1 1.5688(14) . ?
C12 C13 1.3960(14) . ?
C13 C14 1.3866(17) . ?
C13 H13 0.95 . ?
C14 C15 1.3868(16) . ?
C14 H14 0.95 . ?
C15 C16 1.3970(14) . ?
C15 H15 0.95 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?

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 C1 120.04(8) . . ?
B1 O2 C9 120.16(8) . . ?
C12 O3 C17 117.58(9) . . ?
C16 O4 C18 117.77(8) . . ?
C2 C1 O1 119.91(9) . . ?
C2 C1 C10 121.64(9) . . ?
O1 C1 C10 118.45(8) . . ?
C1 C2 C3 118.74(9) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.43(9) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.52(9) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C10 C5 C6 117.96(9) . . ?
C10 C5 C4 118.09(9) . . ?
C6 C5 C4 123.96(9) . . ?
C7 C6 C5 120.42(9) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.76(9) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 118.38(9) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 O2 119.78(8) . . ?
C8 C9 C10 121.73(9) . . ?
O2 C9 C10 118.49(8) . . ?
C1 C10 C9 120.68(9) . . ?
C1 C10 C5 119.57(9) . . ?
C9 C10 C5 119.75(9) . . ?
C16 C11 C12 117.94(9) . . ?
C16 C11 B1 121.50(9) . . ?
C12 C11 B1 120.47(9) . . ?
O3 C12 C13 123.90(9) . . ?
O3 C12 C11 114.52(9) . . ?
C13 C12 C11 121.58(10) . . ?
C14 C13 C12 118.50(10) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 121.87(10) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 118.42(10) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
O4 C16 C11 114.59(8) . . ?
O4 C16 C15 123.72(9) . . ?
C11 C16 C15 121.67(9) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 B1 O1 122.16(9) . . ?
O2 B1 C11 120.25(9) . . ?
O1 B1 C11 117.58(9) . . ?

####################################################################### 
# 
# 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_23a
_database_code_depnum_ccdc_archive 'CCDC 1962519'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_23a                 
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.175 Check 
RESPONSE: Due to weak diffraction of high angle data.
;
_vrf_PLAT911_23a                 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         59 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2019-09-09T14:29:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C114 H88 B5 Cl4 N8 O11'
_chemical_formula_weight         1941.77

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.7300(2)
_cell_length_b                   13.2386(2)
_cell_length_c                   15.2532(2)
_cell_angle_alpha                84.4240(10)
_cell_angle_beta                 74.9410(10)
_cell_angle_gamma                88.5980(10)
_cell_volume                     2470.56(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    188(2)
_cell_measurement_reflns_used    34647
_cell_measurement_theta_min      2.985
_cell_measurement_theta_max      76.815

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.032
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             1009
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 8 -2 0.0131
1 -1 -9 0.0649
8 -1 1 0.0195
-8 1 -1 0.0136
2 2 10 0.083
-4 -7 1 0.0132
5 -6 1 0.0154


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.627
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.753
_shelx_estimated_absorpt_T_max   0.95

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      188(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0970784
_diffrn_orient_matrix_ub_12      0.0587818
_diffrn_orient_matrix_ub_13      -0.0225749
_diffrn_orient_matrix_ub_21      0.0681808
_diffrn_orient_matrix_ub_22      0.0981554
_diffrn_orient_matrix_ub_23      -0.0228214
_diffrn_orient_matrix_ub_31      0.0404063
_diffrn_orient_matrix_ub_32      -0.0241071
_diffrn_orient_matrix_ub_33      -0.1000322
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_number            64243
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.013
_diffrn_reflns_theta_max         77.356
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_reflns_Friedel_coverage         0
_reflns_number_total             10099
_reflns_number_gt                8210
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.5937P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10099
_refine_ls_number_parameters     737
_refine_ls_number_restraints     868
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.033

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The interstitial benzene ring (C47 < C52) was disordered and split over two
 sites A and B. To help maintain reasonable ADP values and C-C bond lengths, 
 SIMU, RIGU, and AFIX 66 restraints and constraints were applied. Also, the 
 1,8-naphthalenediol complexed to a B-OH group was disordered about 
 an inversion center and all of the SOF values of the atoms were set to 0.5. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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 0.90895(3) 0.25032(3) -0.04854(3) 0.04667(10) Uani 1 1 d . . . . .
Cl2 Cl 0.22293(3) 0.53644(3) 0.38886(3) 0.05342(12) Uani 1 1 d . . . . .
O1 O 0.28585(11) 0.30472(8) 0.81146(8) 0.0576(3) Uani 1 1 d . . . . .
O2 O 0.28678(12) 0.14151(8) 0.74911(8) 0.0594(3) Uani 1 1 d . . . . .
O3 O 0.28903(9) 0.23085(9) 0.25623(8) 0.0512(3) Uani 1 1 d . . . . .
O4 O 0.10843(10) 0.20277(10) 0.35809(8) 0.0591(3) Uani 1 1 d . . . . .
N1 N 0.37247(10) 0.29334(9) 0.64689(9) 0.0428(3) Uani 1 1 d . . . . .
N2 N 0.18166(11) 0.28221(10) 0.69876(9) 0.0451(3) Uani 1 1 d . . . . .
N3 N 0.13399(11) 0.31382(10) 0.21360(10) 0.0490(3) Uani 1 1 d . . . . .
N4 N 0.14729(11) 0.13595(10) 0.20720(9) 0.0463(3) Uani 1 1 d . . . . .
C1 C 0.31573(14) 0.25741(12) 0.88528(11) 0.0460(4) Uani 1 1 d . . . . .
C2 C 0.32447(13) 0.15063(12) 0.89375(10) 0.0446(4) Uani 1 1 d . . . . .
C3 C 0.30603(14) 0.09259(12) 0.82640(11) 0.0477(4) Uani 1 1 d . . . . .
C4 C 0.30894(17) -0.01098(13) 0.83644(13) 0.0589(5) Uani 1 1 d . . . . .
H4 H 0.293761 -0.049232 0.791593 0.071 Uiso 1 1 calc R U . . .
C5 C 0.33476(18) -0.06027(14) 0.91422(14) 0.0662(5) Uani 1 1 d . . . . .
H5 H 0.335867 -0.13233 0.922061 0.079 Uiso 1 1 calc R U . . .
C6 C 0.35817(17) -0.00630(15) 0.97841(13) 0.0634(5) Uani 1 1 d . . . . .
H6 H 0.378281 -0.041254 1.028994 0.076 Uiso 1 1 calc R U . . .
C7 C 0.35306(14) 0.10031(13) 0.97100(11) 0.0513(4) Uani 1 1 d . . . . .
C8 C 0.37449(16) 0.16122(16) 1.03591(12) 0.0610(5) Uani 1 1 d . . . . .
H8 H 0.395457 0.129814 1.087466 0.073 Uiso 1 1 calc R U . . .
C9 C 0.36543(16) 0.26407(15) 1.02532(12) 0.0597(5) Uani 1 1 d . . . . .
H9 H 0.379844 0.303175 1.069929 0.072 Uiso 1 1 calc R U . . .
C10 C 0.33516(15) 0.31379(14) 0.94971(12) 0.0532(4) Uani 1 1 d . . . . .
H10 H 0.328361 0.385588 0.943638 0.064 Uiso 1 1 calc R U . . .
C11 C 0.48048(14) 0.29662(13) 0.63519(13) 0.0531(4) Uani 1 1 d . . . . .
H11 H 0.511214 0.269284 0.682865 0.064 Uiso 1 1 calc R U . . .
C12 C 0.54717(14) 0.33924(13) 0.55470(14) 0.0554(4) Uani 1 1 d . . . . .
H12 H 0.623534 0.342443 0.547041 0.067 Uiso 1 1 calc R U . . .
C13 C 0.50219(13) 0.37724(12) 0.48534(13) 0.0488(4) Uani 1 1 d . . . . .
H13 H 0.54788 0.404684 0.428823 0.059 Uiso 1 1 calc R U . . .
C14 C 0.39009(12) 0.37551(11) 0.49785(11) 0.0422(3) Uani 1 1 d . . . . .
H14 H 0.357756 0.402662 0.451106 0.051 Uiso 1 1 calc R U . . .
C15 C 0.32787(12) 0.33331(10) 0.57987(10) 0.0371(3) Uani 1 1 d . . . . .
C16 C 0.20919(12) 0.32470(11) 0.61171(10) 0.0394(3) Uani 1 1 d . . . . .
C17 C 0.13188(13) 0.35588(12) 0.56669(12) 0.0475(4) Uani 1 1 d . . . . .
H17 H 0.151671 0.386039 0.505575 0.057 Uiso 1 1 calc R U . . .
C18 C 0.02357(14) 0.34148(14) 0.61421(15) 0.0596(5) Uani 1 1 d . . . . .
H18 H -0.032482 0.362357 0.585723 0.071 Uiso 1 1 calc R U . . .
C19 C -0.00266(15) 0.29698(15) 0.70261(15) 0.0634(5) Uani 1 1 d . . . . .
H19 H -0.076768 0.286581 0.734777 0.076 Uiso 1 1 calc R U . . .
C20 C 0.07786(15) 0.26772(14) 0.74415(13) 0.0580(4) Uani 1 1 d . . . . .
H20 H 0.059777 0.237178 0.805158 0.07 Uiso 1 1 calc R U . . .
C21 C 0.33518(14) 0.19855(11) 0.32532(11) 0.0453(4) Uani 1 1 d . . . . .
C22 C 0.26768(15) 0.15801(11) 0.40937(11) 0.0478(4) Uani 1 1 d . . . . .
C23 C 0.15322(16) 0.15694(13) 0.42419(12) 0.0529(4) Uani 1 1 d . . . . .
C24 C 0.0874(2) 0.11393(15) 0.50411(13) 0.0682(5) Uani 1 1 d . . . . .
H24 H 0.010786 0.11218 0.513035 0.082 Uiso 1 1 calc R U . . .
C25 C 0.1354(3) 0.07228(16) 0.57295(14) 0.0821(7) Uani 1 1 d . . . . .
H25 H 0.090009 0.042259 0.628583 0.098 Uiso 1 1 calc R U . . .
C26 C 0.2444(3) 0.07389(15) 0.56197(14) 0.0786(7) Uani 1 1 d . . . . .
H26 H 0.273819 0.045577 0.610103 0.094 Uiso 1 1 calc R U . . .
C27 C 0.31538(19) 0.11713(12) 0.47979(13) 0.0606(5) Uani 1 1 d . . . . .
C28 C 0.4296(2) 0.12275(14) 0.46306(16) 0.0707(6) Uani 1 1 d . . . . .
H28 H 0.46348 0.095858 0.508922 0.085 Uiso 1 1 calc R U . . .
C29 C 0.49201(18) 0.16604(14) 0.38239(17) 0.0664(5) Uani 1 1 d . . . . .
H29 H 0.568474 0.170523 0.373606 0.08 Uiso 1 1 calc R U . . .
C30 C 0.44549(15) 0.20432(12) 0.31167(14) 0.0542(4) Uani 1 1 d . . . . .
H30 H 0.489995 0.233683 0.255372 0.065 Uiso 1 1 calc R U . . .
C31 C 0.14156(16) 0.41138(14) 0.22787(14) 0.0604(5) Uani 1 1 d . . . . .
H31 H 0.168325 0.428497 0.277155 0.073 Uiso 1 1 calc R U . . .
C32 C 0.1105(2) 0.48667(15) 0.17104(17) 0.0757(6) Uani 1 1 d . . . . .
H32 H 0.116055 0.555936 0.18073 0.091 Uiso 1 1 calc R U . . .
C33 C 0.0715(2) 0.46117(15) 0.10027(18) 0.0844(7) Uani 1 1 d . . . . .
H33 H 0.050022 0.51307 0.060966 0.101 Uiso 1 1 calc R U . . .
C34 C 0.0633(2) 0.36032(14) 0.08569(16) 0.0731(6) Uani 1 1 d . . . . .
H34 H 0.036031 0.341864 0.037074 0.088 Uiso 1 1 calc R U . . .
C35 C 0.09592(15) 0.28768(13) 0.14422(13) 0.0522(4) Uani 1 1 d . . . . .
C36 C 0.10133(14) 0.17736(12) 0.14162(12) 0.0499(4) Uani 1 1 d . . . . .
C37 C 0.06757(17) 0.11859(13) 0.08444(14) 0.0615(5) Uani 1 1 d . . . . .
H37 H 0.034438 0.148276 0.039048 0.074 Uiso 1 1 calc R U . . .
C38 C 0.08350(17) 0.01470(14) 0.09525(15) 0.0651(5) Uani 1 1 d . . . . .
H38 H 0.061722 -0.027939 0.056499 0.078 Uiso 1 1 calc R U . . .
C39 C 0.13093(16) -0.02703(13) 0.16215(14) 0.0602(5) Uani 1 1 d . . . . .
H39 H 0.141999 -0.098238 0.169609 0.072 Uiso 1 1 calc R U . . .
C40 C 0.16198(14) 0.03541(13) 0.21788(13) 0.0531(4) Uani 1 1 d . . . . .
H40 H 0.19412 0.007037 0.264353 0.064 Uiso 1 1 calc R U . . .
C41 C 0.30446(15) 0.88490(13) 0.37549(13) 0.0545(4) Uani 1 1 d . . . . .
H41 H 0.280269 0.905033 0.435567 0.065 Uiso 1 1 calc R U . . .
C42 C 0.25955(14) 0.80094(13) 0.35181(13) 0.0515(4) Uani 1 1 d . . . . .
H42 H 0.20382 0.763464 0.395615 0.062 Uiso 1 1 calc R U . . .
C43 C 0.29533(14) 0.77148(13) 0.26498(12) 0.0500(4) Uani 1 1 d . . . . .
H43 H 0.265701 0.712505 0.249618 0.06 Uiso 1 1 calc R U . . .
C44 C 0.37401(14) 0.82707(13) 0.20002(12) 0.0503(4) Uani 1 1 d . . . . .
H44 H 0.397618 0.807319 0.139772 0.06 Uiso 1 1 calc R U . . .
C45 C 0.41821(14) 0.91179(12) 0.22339(13) 0.0524(4) Uani 1 1 d . . . . .
H45 H 0.471673 0.951008 0.178867 0.063 Uiso 1 1 calc R U . . .
C46 C 0.38478(15) 0.93927(12) 0.31107(13) 0.0543(4) Uani 1 1 d . . . . .
H46 H 0.417203 0.99606 0.327394 0.065 Uiso 1 1 calc R U . . .
C47A C 0.8404(4) 0.2164(4) 0.3008(4) 0.0713(14) Uani 0.500(9) 1 d G U P A 1
H47A H 0.854981 0.14563 0.305088 0.086 Uiso 0.500(9) 1 calc R U P A 1
C48A C 0.8238(5) 0.2650(4) 0.2206(3) 0.0696(13) Uani 0.500(9) 1 d G U P A 1
H48A H 0.826896 0.227405 0.170006 0.083 Uiso 0.500(9) 1 calc R U P A 1
C49A C 0.8025(6) 0.3686(4) 0.2144(4) 0.0947(17) Uani 0.500(9) 1 d G U P A 1
H49A H 0.791089 0.401756 0.159557 0.114 Uiso 0.500(9) 1 calc R U P A 1
C50A C 0.7979(5) 0.4235(4) 0.2884(5) 0.0928(16) Uani 0.500(9) 1 d G U P A 1
H50A H 0.783366 0.494333 0.284191 0.111 Uiso 0.500(9) 1 calc R U P A 1
C51A C 0.8146(5) 0.3750(6) 0.3687(3) 0.0793(16) Uani 0.500(9) 1 d G U P A 1
H51A H 0.811451 0.41256 0.419274 0.095 Uiso 0.500(9) 1 calc R U P A 1
C52A C 0.8359(4) 0.2714(6) 0.3749(3) 0.0746(16) Uani 0.500(9) 1 d G U P A 1
H52A H 0.847258 0.238209 0.429724 0.09 Uiso 0.500(9) 1 calc R U P A 1
C47B C 0.8242(5) 0.1993(3) 0.2839(4) 0.0718(14) Uani 0.500(9) 1 d G U P A 2
H47B H 0.836083 0.130764 0.270169 0.086 Uiso 0.500(9) 1 calc R U P A 2
C48B C 0.7870(6) 0.2694(5) 0.2249(3) 0.0896(17) Uani 0.500(9) 1 d G U P A 2
H48B H 0.773491 0.248786 0.170889 0.108 Uiso 0.500(9) 1 calc R U P A 2
C49B C 0.7696(6) 0.3696(4) 0.2450(5) 0.0913(16) Uani 0.500(9) 1 d G U P A 2
H49B H 0.744176 0.417478 0.204695 0.11 Uiso 0.500(9) 1 calc R U P A 2
C50B C 0.7894(5) 0.3997(4) 0.3241(5) 0.0847(15) Uani 0.500(9) 1 d G U P A 2
H50B H 0.777451 0.468149 0.33778 0.102 Uiso 0.500(9) 1 calc R U P A 2
C51B C 0.8265(4) 0.3296(5) 0.3830(3) 0.0733(15) Uani 0.500(9) 1 d G U P A 2
H51B H 0.840043 0.350129 0.43706 0.088 Uiso 0.500(9) 1 calc R U P A 2
C52B C 0.8439(4) 0.2294(5) 0.3629(3) 0.0674(13) Uani 0.500(9) 1 d G U P A 2
H52B H 0.869359 0.181436 0.403256 0.081 Uiso 0.500(9) 1 calc R U P A 2
O5 O 0.4396(2) 0.4857(2) 0.29026(16) 0.0591(6) Uani 0.5 1 d D . P B -1
H5A H 0.3736(15) 0.5130(18) 0.3163(16) 0.089 Uiso 1 1 d D U . C -1
O6 O 0.5430(6) 0.4342(6) 0.1530(4) 0.0465(12) Uani 0.5 1 d . . P B -1
O7 O 0.3927(7) 0.5479(6) 0.1545(4) 0.0487(11) Uani 0.5 1 d . . P B -1
C53 C 0.5674(3) 0.4354(2) 0.0597(3) 0.0408(6) Uani 0.5 1 d . . P B -1
C54 C 0.6499(6) 0.3785(7) 0.0157(5) 0.0454(14) Uani 0.5 1 d . . P B -1
H54 H 0.691038 0.336508 0.048566 0.055 Uiso 0.5 1 calc R U P B -1
C55 C 0.6738(3) 0.3828(3) -0.0803(3) 0.0561(9) Uani 0.5 1 d . . P B -1
H55 H 0.731752 0.342745 -0.111821 0.067 Uiso 0.5 1 calc R U P B -1
C56 C 0.6162(10) 0.4425(10) -0.1292(6) 0.0547(17) Uani 0.5 1 d . . P B -1
H56 H 0.63362 0.443262 -0.1937 0.066 Uiso 0.5 1 calc R U P B -1
C57 C 0.5299(3) 0.5037(2) -0.0832(2) 0.0451(7) Uani 0.5 1 d . . P B -1
C58 C 0.5034(10) 0.4989(10) 0.0139(5) 0.0366(13) Uani 0.5 1 d . . P B -1
C59 C 0.4175(3) 0.5559(2) 0.0601(3) 0.0416(7) Uani 0.5 1 d . . P B -1
C60 C 0.3571(7) 0.6176(7) 0.0161(5) 0.0496(16) Uani 0.5 1 d . . P B -1
H60 H 0.297853 0.655203 0.049057 0.06 Uiso 0.5 1 calc R U P B -1
C61 C 0.3849(4) 0.6245(3) -0.0809(4) 0.0561(9) Uani 0.5 1 d . . P B -1
H61 H 0.344317 0.6686 -0.112697 0.067 Uiso 0.5 1 calc R U P B -1
C62 C 0.4672(11) 0.5703(10) -0.1290(8) 0.0565(19) Uani 0.5 1 d . . P B -1
H62 H 0.483565 0.576422 -0.193658 0.068 Uiso 0.5 1 calc R U P B -1
B3 B 0.4576(3) 0.4895(3) 0.1996(3) 0.0445(8) Uani 0.5 1 d . . P B -1
B1 B 0.28300(18) 0.24932(14) 0.73710(13) 0.0496(4) Uani 1 1 d . . . . .
B2 B 0.17516(16) 0.21984(15) 0.26800(13) 0.0489(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 1.3706(19) . ?
O1 B1 1.418(2) . ?
O2 C3 1.3649(18) . ?
O2 B1 1.422(2) . ?
O3 C21 1.3640(18) . ?
O3 B2 1.423(2) . ?
O4 C23 1.368(2) . ?
O4 B2 1.416(2) . ?
N1 C11 1.341(2) . ?
N1 C15 1.3524(18) . ?
N1 B1 1.610(2) . ?
N2 C20 1.332(2) . ?
N2 C16 1.351(2) . ?
N2 B1 1.585(2) . ?
N3 C31 1.340(2) . ?
N3 C35 1.349(2) . ?
N3 B2 1.582(2) . ?
N4 C40 1.340(2) . ?
N4 C36 1.3511(19) . ?
N4 B2 1.615(2) . ?
C1 C10 1.365(2) . ?
C1 C2 1.411(2) . ?
C2 C3 1.410(2) . ?
C2 C7 1.422(2) . ?
C3 C4 1.365(2) . ?
C4 C5 1.408(2) . ?
C4 H4 0.95 . ?
C5 C6 1.362(3) . ?
C5 H5 0.95 . ?
C6 C7 1.406(3) . ?
C6 H6 0.95 . ?
C7 C8 1.418(3) . ?
C8 C9 1.361(3) . ?
C8 H8 0.95 . ?
C9 C10 1.408(3) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.376(3) . ?
C11 H11 0.95 . ?
C12 C13 1.377(2) . ?
C12 H12 0.95 . ?
C13 C14 1.390(2) . ?
C13 H13 0.95 . ?
C14 C15 1.369(2) . ?
C14 H14 0.95 . ?
C15 C16 1.465(2) . ?
C16 C17 1.374(2) . ?
C17 C18 1.389(2) . ?
C17 H17 0.95 . ?
C18 C19 1.378(3) . ?
C18 H18 0.95 . ?
C19 C20 1.368(3) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 C30 1.368(2) . ?
C21 C22 1.409(2) . ?
C22 C23 1.416(3) . ?
C22 C27 1.423(2) . ?
C23 C24 1.367(3) . ?
C24 C25 1.408(3) . ?
C24 H24 0.95 . ?
C25 C26 1.355(4) . ?
C25 H25 0.95 . ?
C26 C27 1.419(3) . ?
C26 H26 0.95 . ?
C27 C28 1.412(3) . ?
C28 C29 1.360(3) . ?
C28 H28 0.95 . ?
C29 C30 1.408(3) . ?
C29 H29 0.95 . ?
C30 H30 0.95 . ?
C31 C32 1.375(3) . ?
C31 H31 0.95 . ?
C32 C33 1.372(3) . ?
C32 H32 0.95 . ?
C33 C34 1.386(3) . ?
C33 H33 0.95 . ?
C34 C35 1.379(2) . ?
C34 H34 0.95 . ?
C35 C36 1.464(2) . ?
C36 C37 1.376(2) . ?
C37 C38 1.385(2) . ?
C37 H37 0.95 . ?
C38 C39 1.380(2) . ?
C38 H38 0.95 . ?
C39 C40 1.375(3) . ?
C39 H39 0.95 . ?
C40 H40 0.95 . ?
C41 C46 1.380(3) . ?
C41 C42 1.382(2) . ?
C41 H41 0.95 . ?
C42 C43 1.376(3) . ?
C42 H42 0.95 . ?
C43 C44 1.380(2) . ?
C43 H43 0.95 . ?
C44 C45 1.384(2) . ?
C44 H44 0.95 . ?
C45 C46 1.376(3) . ?
C45 H45 0.95 . ?
C46 H46 0.95 . ?
C47A C48A 1.39 . ?
C47A C52A 1.39 . ?
C47A H47A 0.95 . ?
C48A C49A 1.39 . ?
C48A H48A 0.95 . ?
C49A C50A 1.39 . ?
C49A H49A 0.95 . ?
C50A C51A 1.39 . ?
C50A H50A 0.95 . ?
C51A C52A 1.39 . ?
C51A H51A 0.95 . ?
C52A H52A 0.95 . ?
C47B C48B 1.39 . ?
C47B C52B 1.39 . ?
C47B H47B 0.95 . ?
C48B C49B 1.39 . ?
C48B H48B 0.95 . ?
C49B C50B 1.39 . ?
C49B H49B 0.95 . ?
C50B C51B 1.39 . ?
C50B H50B 0.95 . ?
C51B C52B 1.39 . ?
C51B H51B 0.95 . ?
C52B H52B 0.95 . ?
O5 B3 1.338(4) . ?
O5 H5A 0.914(16) . ?
O6 B3 1.372(8) . ?
O6 C53 1.375(6) . ?
O7 B3 1.383(6) . ?
O7 C59 1.385(6) . ?
C53 C54 1.346(9) . ?
C53 C58 1.416(9) . ?
C54 C55 1.412(7) . ?
C54 H54 0.95 . ?
C55 C56 1.364(9) . ?
C55 H55 0.95 . ?
C56 C57 1.422(13) . ?
C56 H56 0.95 . ?
C57 C58 1.426(7) . ?
C57 C62 1.427(11) . ?
C58 C59 1.387(12) . ?
C59 C60 1.357(7) . ?
C60 C61 1.423(7) . ?
C60 H60 0.95 . ?
C61 C62 1.348(14) . ?
C61 H61 0.95 . ?
C62 H62 0.95 . ?

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 120.00(13) . . ?
C3 O2 B1 120.80(13) . . ?
C21 O3 B2 120.29(13) . . ?
C23 O4 B2 118.55(14) . . ?
C11 N1 C15 120.13(14) . . ?
C11 N1 B1 126.93(13) . . ?
C15 N1 B1 112.89(12) . . ?
C20 N2 C16 121.08(15) . . ?
C20 N2 B1 125.22(15) . . ?
C16 N2 B1 113.66(13) . . ?
C31 N3 C35 121.10(15) . . ?
C31 N3 B2 125.58(14) . . ?
C35 N3 B2 113.16(14) . . ?
C40 N4 C36 120.40(14) . . ?
C40 N4 B2 127.24(13) . . ?
C36 N4 B2 112.33(13) . . ?
C10 C1 O1 119.73(15) . . ?
C10 C1 C2 121.15(15) . . ?
O1 C1 C2 119.11(14) . . ?
C3 C2 C1 121.08(14) . . ?
C3 C2 C7 119.17(15) . . ?
C1 C2 C7 119.75(15) . . ?
O2 C3 C4 119.69(15) . . ?
O2 C3 C2 118.98(14) . . ?
C4 C3 C2 121.32(15) . . ?
C3 C4 C5 119.05(17) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.06(17) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.07(16) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 124.12(16) . . ?
C6 C7 C2 118.20(16) . . ?
C8 C7 C2 117.68(16) . . ?
C9 C8 C7 120.88(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.45(16) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C1 C10 C9 119.08(17) . . ?
C1 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C12 120.54(15) . . ?
N1 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 119.40(15) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 120.16(16) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 117.72(14) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
N1 C15 C14 122.00(13) . . ?
N1 C15 C16 109.11(13) . . ?
C14 C15 C16 128.87(13) . . ?
N2 C16 C17 121.71(15) . . ?
N2 C16 C15 109.28(12) . . ?
C17 C16 C15 128.98(14) . . ?
C16 C17 C18 117.25(17) . . ?
C16 C17 H17 121.4 . . ?
C18 C17 H17 121.4 . . ?
C19 C18 C17 120.08(17) . . ?
C19 C18 H18 120 . . ?
C17 C18 H18 120 . . ?
C20 C19 C18 120.11(17) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
N2 C20 C19 119.76(18) . . ?
N2 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
O3 C21 C30 119.84(16) . . ?
O3 C21 C22 118.91(14) . . ?
C30 C21 C22 121.24(15) . . ?
C21 C22 C23 120.73(14) . . ?
C21 C22 C27 119.52(17) . . ?
C23 C22 C27 119.74(17) . . ?
C24 C23 O4 119.98(18) . . ?
C24 C23 C22 121.10(18) . . ?
O4 C23 C22 118.89(15) . . ?
C23 C24 C25 118.8(2) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C26 C25 C24 121.8(2) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 121.1(2) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C28 C27 C26 124.74(19) . . ?
C28 C27 C22 117.80(19) . . ?
C26 C27 C22 117.5(2) . . ?
C29 C28 C27 121.11(17) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 121.31(19) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C21 C30 C29 118.93(19) . . ?
C21 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
N3 C31 C32 119.89(17) . . ?
N3 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 119.62(19) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C34 120.53(19) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C35 C34 C33 117.66(18) . . ?
C35 C34 H34 121.2 . . ?
C33 C34 H34 121.2 . . ?
N3 C35 C34 121.20(16) . . ?
N3 C35 C36 109.77(14) . . ?
C34 C35 C36 128.97(16) . . ?
N4 C36 C37 121.67(15) . . ?
N4 C36 C35 109.22(14) . . ?
C37 C36 C35 129.11(15) . . ?
C36 C37 C38 117.81(16) . . ?
C36 C37 H37 121.1 . . ?
C38 C37 H37 121.1 . . ?
C39 C38 C37 120.19(17) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C40 C39 C38 119.38(16) . . ?
C40 C39 H39 120.3 . . ?
C38 C39 H39 120.3 . . ?
N4 C40 C39 120.54(15) . . ?
N4 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C46 C41 C42 119.42(17) . . ?
C46 C41 H41 120.3 . . ?
C42 C41 H41 120.3 . . ?
C43 C42 C41 120.18(16) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C42 C43 C44 120.41(16) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C43 C44 C45 119.45(17) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
C46 C45 C44 120.04(16) . . ?
C46 C45 H45 120 . . ?
C44 C45 H45 120 . . ?
C45 C46 C41 120.46(16) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
C48A C47A C52A 120 . . ?
C48A C47A H47A 120 . . ?
C52A C47A H47A 120 . . ?
C49A C48A C47A 120 . . ?
C49A C48A H48A 120 . . ?
C47A C48A H48A 120 . . ?
C50A C49A C48A 120 . . ?
C50A C49A H49A 120 . . ?
C48A C49A H49A 120 . . ?
C49A C50A C51A 120 . . ?
C49A C50A H50A 120 . . ?
C51A C50A H50A 120 . . ?
C52A C51A C50A 120 . . ?
C52A C51A H51A 120 . . ?
C50A C51A H51A 120 . . ?
C51A C52A C47A 120 . . ?
C51A C52A H52A 120 . . ?
C47A C52A H52A 120 . . ?
C48B C47B C52B 120 . . ?
C48B C47B H47B 120 . . ?
C52B C47B H47B 120 . . ?
C49B C48B C47B 120 . . ?
C49B C48B H48B 120 . . ?
C47B C48B H48B 120 . . ?
C48B C49B C50B 120 . . ?
C48B C49B H49B 120 . . ?
C50B C49B H49B 120 . . ?
C51B C50B C49B 120 . . ?
C51B C50B H50B 120 . . ?
C49B C50B H50B 120 . . ?
C50B C51B C52B 120 . . ?
C50B C51B H51B 120 . . ?
C52B C51B H51B 120 . . ?
C51B C52B C47B 120 . . ?
C51B C52B H52B 120 . . ?
C47B C52B H52B 120 . . ?
B3 O5 H5A 111.2(16) . . ?
B3 O6 C53 121.1(5) . . ?
B3 O7 C59 119.8(6) . . ?
C54 C53 O6 119.9(5) . . ?
C54 C53 C58 123.0(6) . . ?
O6 C53 C58 117.1(6) . . ?
C53 C54 C55 118.4(6) . . ?
C53 C54 H54 120.8 . . ?
C55 C54 H54 120.8 . . ?
C56 C55 C54 122.0(7) . . ?
C56 C55 H55 119 . . ?
C54 C55 H55 119 . . ?
C55 C56 C57 119.7(7) . . ?
C55 C56 H56 120.1 . . ?
C57 C56 H56 120.1 . . ?
C56 C57 C58 119.0(6) . . ?
C56 C57 C62 123.5(7) . . ?
C58 C57 C62 117.6(7) . . ?
C59 C58 C53 122.4(5) . . ?
C59 C58 C57 119.8(6) . . ?
C53 C58 C57 117.9(8) . . ?
C60 C59 O7 119.5(5) . . ?
C60 C59 C58 122.2(5) . . ?
O7 C59 C58 118.2(4) . . ?
C59 C60 C61 118.2(7) . . ?
C59 C60 H60 120.9 . . ?
C61 C60 H60 120.9 . . ?
C62 C61 C60 121.8(6) . . ?
C62 C61 H61 119.1 . . ?
C60 C61 H61 119.1 . . ?
C61 C62 C57 120.4(8) . . ?
C61 C62 H62 119.8 . . ?
C57 C62 H62 119.8 . . ?
O5 B3 O6 117.7(4) . . ?
O5 B3 O7 121.0(4) . . ?
O6 B3 O7 121.3(5) . . ?
O1 B1 O2 118.62(14) . . ?
O1 B1 N2 110.67(15) . . ?
O2 B1 N2 108.76(14) . . ?
O1 B1 N1 110.04(14) . . ?
O2 B1 N1 111.25(15) . . ?
N2 B1 N1 94.95(11) . . ?
O4 B2 O3 117.86(14) . . ?
O4 B2 N3 111.44(15) . . ?
O3 B2 N3 108.35(14) . . ?
O4 B2 N4 109.07(14) . . ?
O3 B2 N4 112.42(15) . . ?
N3 B2 N4 95.45(12) . . ?

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
B1 O1 C1 C10 169.59(17) . . . . ?
B1 O1 C1 C2 -11.2(2) . . . . ?
C10 C1 C2 C3 -178.99(16) . . . . ?
O1 C1 C2 C3 1.8(2) . . . . ?
C10 C1 C2 C7 0.6(3) . . . . ?
O1 C1 C2 C7 -178.62(15) . . . . ?
B1 O2 C3 C4 179.80(18) . . . . ?
B1 O2 C3 C2 -1.3(3) . . . . ?
C1 C2 C3 O2 4.5(2) . . . . ?
C7 C2 C3 O2 -175.06(15) . . . . ?
C1 C2 C3 C4 -176.63(17) . . . . ?
C7 C2 C3 C4 3.8(3) . . . . ?
O2 C3 C4 C5 176.56(18) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C7 2.6(3) . . . . ?
C5 C6 C7 C8 178.9(2) . . . . ?
C5 C6 C7 C2 -1.0(3) . . . . ?
C3 C2 C7 C6 -2.1(3) . . . . ?
C1 C2 C7 C6 178.33(16) . . . . ?
C3 C2 C7 C8 177.98(16) . . . . ?
C1 C2 C7 C8 -1.6(2) . . . . ?
C6 C7 C8 C9 -178.42(19) . . . . ?
C2 C7 C8 C9 1.5(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
O1 C1 C10 C9 179.78(16) . . . . ?
C2 C1 C10 C9 0.6(3) . . . . ?
C8 C9 C10 C1 -0.7(3) . . . . ?
C15 N1 C11 C12 -0.9(2) . . . . ?
B1 N1 C11 C12 -178.18(16) . . . . ?
N1 C11 C12 C13 -1.0(3) . . . . ?
C11 C12 C13 C14 2.1(3) . . . . ?
C12 C13 C14 C15 -1.3(2) . . . . ?
C11 N1 C15 C14 1.8(2) . . . . ?
B1 N1 C15 C14 179.44(14) . . . . ?
C11 N1 C15 C16 -177.01(14) . . . . ?
B1 N1 C15 C16 0.63(17) . . . . ?
C13 C14 C15 N1 -0.7(2) . . . . ?
C13 C14 C15 C16 177.87(15) . . . . ?
C20 N2 C16 C17 0.8(2) . . . . ?
B1 N2 C16 C17 178.64(15) . . . . ?
C20 N2 C16 C15 178.77(14) . . . . ?
B1 N2 C16 C15 -3.42(17) . . . . ?
N1 C15 C16 N2 1.72(17) . . . . ?
C14 C15 C16 N2 -176.99(15) . . . . ?
N1 C15 C16 C17 179.46(15) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
N2 C16 C17 C18 -0.3(2) . . . . ?
C15 C16 C17 C18 -177.83(15) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C16 N2 C20 C19 -0.6(3) . . . . ?
B1 N2 C20 C19 -178.11(16) . . . . ?
C18 C19 C20 N2 -0.2(3) . . . . ?
B2 O3 C21 C30 176.39(16) . . . . ?
B2 O3 C21 C22 -2.5(2) . . . . ?
O3 C21 C22 C23 -4.2(2) . . . . ?
C30 C21 C22 C23 176.91(16) . . . . ?
O3 C21 C22 C27 175.37(14) . . . . ?
C30 C21 C22 C27 -3.5(2) . . . . ?
B2 O4 C23 C24 -161.77(17) . . . . ?
B2 O4 C23 C22 20.3(2) . . . . ?
C21 C22 C23 C24 177.24(16) . . . . ?
C27 C22 C23 C24 -2.3(2) . . . . ?
C21 C22 C23 O4 -4.8(2) . . . . ?
C27 C22 C23 O4 175.58(14) . . . . ?
O4 C23 C24 C25 -176.51(17) . . . . ?
C22 C23 C24 C25 1.4(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C27 -0.5(3) . . . . ?
C25 C26 C27 C28 179.39(19) . . . . ?
C25 C26 C27 C22 -0.4(3) . . . . ?
C21 C22 C27 C28 2.4(2) . . . . ?
C23 C22 C27 C28 -178.00(15) . . . . ?
C21 C22 C27 C26 -177.78(15) . . . . ?
C23 C22 C27 C26 1.8(2) . . . . ?
C26 C27 C28 C29 -179.63(18) . . . . ?
C22 C27 C28 C29 0.2(3) . . . . ?
C27 C28 C29 C30 -1.8(3) . . . . ?
O3 C21 C30 C29 -176.94(15) . . . . ?
C22 C21 C30 C29 1.9(2) . . . . ?
C28 C29 C30 C21 0.7(3) . . . . ?
C35 N3 C31 C32 -0.2(3) . . . . ?
B2 N3 C31 C32 174.79(19) . . . . ?
N3 C31 C32 C33 0.3(4) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
C32 C33 C34 C35 -0.3(4) . . . . ?
C31 N3 C35 C34 -0.1(3) . . . . ?
B2 N3 C35 C34 -175.72(19) . . . . ?
C31 N3 C35 C36 177.23(17) . . . . ?
B2 N3 C35 C36 1.7(2) . . . . ?
C33 C34 C35 N3 0.4(3) . . . . ?
C33 C34 C35 C36 -176.4(2) . . . . ?
C40 N4 C36 C37 0.5(3) . . . . ?
B2 N4 C36 C37 -177.54(18) . . . . ?
C40 N4 C36 C35 -179.45(16) . . . . ?
B2 N4 C36 C35 2.5(2) . . . . ?
N3 C35 C36 N4 -2.6(2) . . . . ?
C34 C35 C36 N4 174.5(2) . . . . ?
N3 C35 C36 C37 177.4(2) . . . . ?
C34 C35 C36 C37 -5.4(4) . . . . ?
N4 C36 C37 C38 -0.9(3) . . . . ?
C35 C36 C37 C38 179.0(2) . . . . ?
C36 C37 C38 C39 0.6(3) . . . . ?
C37 C38 C39 C40 0.1(3) . . . . ?
C36 N4 C40 C39 0.2(3) . . . . ?
B2 N4 C40 C39 177.92(17) . . . . ?
C38 C39 C40 N4 -0.5(3) . . . . ?
C46 C41 C42 C43 0.5(3) . . . . ?
C41 C42 C43 C44 -1.9(3) . . . . ?
C42 C43 C44 C45 1.2(2) . . . . ?
C43 C44 C45 C46 0.9(2) . . . . ?
C44 C45 C46 C41 -2.3(3) . . . . ?
C42 C41 C46 C45 1.6(3) . . . . ?
C52A C47A C48A C49A 0 . . . . ?
C47A C48A C49A C50A 0 . . . . ?
C48A C49A C50A C51A 0 . . . . ?
C49A C50A C51A C52A 0 . . . . ?
C50A C51A C52A C47A 0 . . . . ?
C48A C47A C52A C51A 0 . . . . ?
C52B C47B C48B C49B 0 . . . . ?
C47B C48B C49B C50B 0 . . . . ?
C48B C49B C50B C51B 0 . . . . ?
C49B C50B C51B C52B 0 . . . . ?
C50B C51B C52B C47B 0 . . . . ?
C48B C47B C52B C51B 0 . . . . ?
B3 O6 C53 C54 -178.3(6) . . . . ?
B3 O6 C53 C58 2.4(11) . . . . ?
O6 C53 C54 C55 -179.0(6) . . . . ?
C58 C53 C54 C55 0.2(12) . . . . ?
C53 C54 C55 C56 0.1(12) . . . . ?
C54 C55 C56 C57 0.7(15) . . . . ?
C55 C56 C57 C58 -1.8(15) . . . . ?
C55 C56 C57 C62 178.4(9) . . . . ?
C54 C53 C58 C59 178.9(8) . . . . ?
O6 C53 C58 C59 -1.8(14) . . . . ?
C54 C53 C58 C57 -1.3(14) . . . . ?
O6 C53 C58 C57 177.9(8) . . . . ?
C56 C57 C58 C59 -178.2(9) . . . . ?
C62 C57 C58 C59 1.7(15) . . . . ?
C56 C57 C58 C53 2.1(14) . . . . ?
C62 C57 C58 C53 -178.1(8) . . . . ?
B3 O7 C59 C60 -176.5(7) . . . . ?
B3 O7 C59 C58 4.3(11) . . . . ?
C53 C58 C59 C60 179.2(9) . . . . ?
C57 C58 C59 C60 -0.5(15) . . . . ?
C53 C58 C59 O7 -1.5(14) . . . . ?
C57 C58 C59 O7 178.7(8) . . . . ?
O7 C59 C60 C61 179.8(7) . . . . ?
C58 C59 C60 C61 -1.0(12) . . . . ?
C59 C60 C61 C62 1.4(12) . . . . ?
C60 C61 C62 C57 -0.2(14) . . . . ?
C56 C57 C62 C61 178.5(9) . . . . ?
C58 C57 C62 C61 -1.3(14) . . . . ?
C53 O6 B3 O5 -179.1(5) . . . . ?
C53 O6 B3 O7 0.3(10) . . . . ?
C59 O7 B3 O5 175.6(5) . . . . ?
C59 O7 B3 O6 -3.8(11) . . . . ?
C1 O1 B1 O2 14.3(3) . . . . ?
C1 O1 B1 N2 140.96(15) . . . . ?
C1 O1 B1 N1 -115.41(15) . . . . ?
C3 O2 B1 O1 -7.9(3) . . . . ?
C3 O2 B1 N2 -135.47(16) . . . . ?
C3 O2 B1 N1 121.25(16) . . . . ?
C20 N2 B1 O1 -65.3(2) . . . . ?
C16 N2 B1 O1 116.98(15) . . . . ?
C20 N2 B1 O2 66.7(2) . . . . ?
C16 N2 B1 O2 -111.05(16) . . . . ?
C20 N2 B1 N1 -178.92(15) . . . . ?
C16 N2 B1 N1 3.38(16) . . . . ?
C11 N1 B1 O1 61.1(2) . . . . ?
C15 N1 B1 O1 -116.39(15) . . . . ?
C11 N1 B1 O2 -72.5(2) . . . . ?
C15 N1 B1 O2 110.07(15) . . . . ?
C11 N1 B1 N2 175.18(15) . . . . ?
C15 N1 B1 N2 -2.27(16) . . . . ?
C23 O4 B2 O3 -26.7(2) . . . . ?
C23 O4 B2 N3 -152.89(14) . . . . ?
C23 O4 B2 N4 103.01(16) . . . . ?
C21 O3 B2 O4 17.8(2) . . . . ?
C21 O3 B2 N3 145.41(14) . . . . ?
C21 O3 B2 N4 -110.40(16) . . . . ?
C31 N3 B2 O4 71.5(2) . . . . ?
C35 N3 B2 O4 -113.15(17) . . . . ?
C31 N3 B2 O3 -59.7(2) . . . . ?
C35 N3 B2 O3 115.61(17) . . . . ?
C31 N3 B2 N4 -175.53(16) . . . . ?
C35 N3 B2 N4 -0.20(18) . . . . ?
C40 N4 B2 O4 -64.4(2) . . . . ?
C36 N4 B2 O4 113.45(16) . . . . ?
C40 N4 B2 O3 68.3(2) . . . . ?
C36 N4 B2 O3 -113.90(16) . . . . ?
C40 N4 B2 N3 -179.31(16) . . . . ?
C36 N4 B2 N3 -1.47(17) . . . . ?

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
_geom_hbond_publ_flag
O5 H5A Cl2 0.914(16) 1.983(18) 2.876(3) 165(2) . yes

####################################################################### 
# 
# 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_14a
_database_code_depnum_ccdc_archive 'CCDC 1962516'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_14a                 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2019-06-24T13:03:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H12 B2 O5'
_chemical_formula_weight         353.92

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4723(2)
_cell_length_b                   8.48060(10)
_cell_length_c                   13.3696(3)
_cell_angle_alpha                87.668(2)
_cell_angle_beta                 82.555(2)
_cell_angle_gamma                67.591(2)
_cell_volume                     776.61(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11566
_cell_measurement_theta_min      3.319
_cell_measurement_theta_max      76.529

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.075
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             364
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0591
2 1 0 0.1185
4 2 7 0.0905
0 0 9 0.0633
1 -4 -2 0.0404
-1 -3 -8 0.0427
-1 4 3 0.032
-4 1 0 0.0763
0 1 8 0.0585
-4 -3 -6 0.0827
-5 -4 0 0.1064
-3 -5 -5 0.0704
-2 -5 1 0.0767
0 -2 8 0.0629
0 2 -8 0.0719
0 -5 -2 0.0363
-1 4 -3 0.0629
4 -1 2 0.0954
1 -1 -8 0.0457


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.786
_shelx_estimated_absorpt_T_max   0.937

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1713976
_diffrn_orient_matrix_ub_12      0.0547392
_diffrn_orient_matrix_ub_13      -0.0372919
_diffrn_orient_matrix_ub_21      0.1384611
_diffrn_orient_matrix_ub_22      -0.1887262
_diffrn_orient_matrix_ub_23      -0.0120625
_diffrn_orient_matrix_ub_31      -0.0442131
_diffrn_orient_matrix_ub_32      0.0001694
_diffrn_orient_matrix_ub_33      -0.1094049
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_number            21542
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.334
_diffrn_reflns_theta_max         77.3
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_reflns_Friedel_coverage         0
_reflns_number_total             3205
_reflns_number_gt                2905
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.1439P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3205
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.095
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.09
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 0.0039 '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'

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 0.84459(10) 0.85711(9) 0.66041(5) 0.02662(18) Uani 1 1 d . . . . .
O2 O 0.80506(10) 0.68593(9) 0.53169(5) 0.02604(18) Uani 1 1 d . . . . .
O3 O 0.67855(10) 0.67929(9) 0.84080(5) 0.02678(18) Uani 1 1 d . . . . .
O4 O 0.93127(10) 0.39717(9) 0.82876(5) 0.02735(18) Uani 1 1 d . . . . .
O5 O 0.87899(11) 0.56972(9) 0.68801(6) 0.03084(19) Uani 1 1 d . . . . .
C1 C 0.79789(14) 0.99778(13) 0.59761(8) 0.0247(2) Uani 1 1 d . . . . .
C2 C 0.74930(13) 0.98121(12) 0.50103(8) 0.0234(2) Uani 1 1 d . . . . .
C3 C 0.75655(14) 0.82275(13) 0.46688(8) 0.0242(2) Uani 1 1 d . . . . .
C4 C 0.71747(15) 0.80276(13) 0.37256(8) 0.0273(2) Uani 1 1 d . . . . .
H4 H 0.728048 0.694419 0.349993 0.033 Uiso 1 1 calc R U . . .
C5 C 0.66113(15) 0.94545(14) 0.30907(8) 0.0301(2) Uani 1 1 d . . . . .
H5 H 0.631529 0.932956 0.243575 0.036 Uiso 1 1 calc R U . . .
C6 C 0.64813(15) 1.10232(14) 0.33999(8) 0.0299(2) Uani 1 1 d . . . . .
H6 H 0.607008 1.197182 0.296305 0.036 Uiso 1 1 calc R U . . .
C7 C 0.69539(14) 1.12409(13) 0.43628(8) 0.0268(2) Uani 1 1 d . . . . .
C8 C 0.69386(15) 1.28038(13) 0.47197(9) 0.0305(2) Uani 1 1 d . . . . .
H8 H 0.655878 1.378786 0.430799 0.037 Uiso 1 1 calc R U . . .
C9 C 0.74648(16) 1.29024(13) 0.56486(9) 0.0318(3) Uani 1 1 d . . . . .
H9 H 0.747174 1.395265 0.586572 0.038 Uiso 1 1 calc R U . . .
C10 C 0.80000(15) 1.14797(13) 0.62961(8) 0.0284(2) Uani 1 1 d . . . . .
H10 H 0.836634 1.156681 0.693969 0.034 Uiso 1 1 calc R U . . .
C11 C 0.63813(15) 0.66132(13) 0.94348(8) 0.0252(2) Uani 1 1 d . . . . .
C12 C 0.74937(14) 0.50824(12) 0.98944(8) 0.0245(2) Uani 1 1 d . . . . .
C13 C 0.89622(15) 0.37474(13) 0.93115(8) 0.0253(2) Uani 1 1 d . . . . .
C14 C 1.00495(15) 0.22584(13) 0.97433(9) 0.0301(2) Uani 1 1 d . . . . .
H14 H 1.100709 0.135769 0.934047 0.036 Uiso 1 1 calc R U . . .
C15 C 0.97260(16) 0.20828(14) 1.07946(9) 0.0334(3) Uani 1 1 d . . . . .
H15 H 1.048835 0.105638 1.110024 0.04 Uiso 1 1 calc R U . . .
C16 C 0.83346(16) 0.33602(15) 1.13890(9) 0.0321(2) Uani 1 1 d . . . . .
H16 H 0.816082 0.321498 1.209846 0.039 Uiso 1 1 calc R U . . .
C17 C 0.71542(15) 0.48956(14) 1.09516(8) 0.0282(2) Uani 1 1 d . . . . .
C18 C 0.56722(16) 0.62683(15) 1.15138(9) 0.0319(2) Uani 1 1 d . . . . .
H18 H 0.541297 0.617605 1.222381 0.038 Uiso 1 1 calc R U . . .
C19 C 0.46146(16) 0.77250(14) 1.10371(9) 0.0324(3) Uani 1 1 d . . . . .
H19 H 0.362657 0.862793 1.142508 0.039 Uiso 1 1 calc R U . . .
C20 C 0.49561(15) 0.79173(13) 0.99854(9) 0.0286(2) Uani 1 1 d . . . . .
H20 H 0.420904 0.893459 0.966631 0.034 Uiso 1 1 calc R U . . .
B1 B 0.84025(17) 0.70831(15) 0.62668(9) 0.0262(2) Uani 1 1 d . . . . .
B2 B 0.83003(17) 0.55110(15) 0.78751(9) 0.0267(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3704(14) . ?
O1 C1 1.3881(12) . ?
O2 B1 1.3647(15) . ?
O2 C3 1.3810(12) . ?
O3 B2 1.3735(14) . ?
O3 C11 1.3819(13) . ?
O4 B2 1.3701(13) . ?
O4 C13 1.3793(13) . ?
O5 B2 1.3524(14) . ?
O5 B1 1.3643(14) . ?
C1 C10 1.3664(14) . ?
C1 C2 1.4122(15) . ?
C2 C3 1.4161(14) . ?
C2 C7 1.4187(14) . ?
C3 C4 1.3619(15) . ?
C4 C5 1.4081(15) . ?
C4 H4 0.95 . ?
C5 C6 1.3734(15) . ?
C5 H5 0.95 . ?
C6 C7 1.4152(16) . ?
C6 H6 0.95 . ?
C7 C8 1.4223(15) . ?
C8 C9 1.3654(17) . ?
C8 H8 0.95 . ?
C9 C10 1.4148(16) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C20 1.3654(15) . ?
C11 C12 1.4138(14) . ?
C12 C13 1.4129(15) . ?
C12 C17 1.4167(15) . ?
C13 C14 1.3667(14) . ?
C14 C15 1.4066(16) . ?
C14 H14 0.95 . ?
C15 C16 1.3723(17) . ?
C15 H15 0.95 . ?
C16 C17 1.4183(15) . ?
C16 H16 0.95 . ?
C17 C18 1.4210(16) . ?
C18 C19 1.3707(16) . ?
C18 H18 0.95 . ?
C19 C20 1.4103(16) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?

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 C1 118.83(9) . . ?
B1 O2 C3 119.26(8) . . ?
B2 O3 C11 119.06(8) . . ?
B2 O4 C13 119.11(8) . . ?
B2 O5 B1 133.03(9) . . ?
C10 C1 O1 120.02(10) . . ?
C10 C1 C2 121.43(10) . . ?
O1 C1 C2 118.55(9) . . ?
C1 C2 C3 120.91(9) . . ?
C1 C2 C7 119.85(9) . . ?
C3 C2 C7 119.23(10) . . ?
C4 C3 O2 119.79(9) . . ?
C4 C3 C2 121.73(10) . . ?
O2 C3 C2 118.48(9) . . ?
C3 C4 C5 118.86(10) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.28(10) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.66(10) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 118.18(9) . . ?
C6 C7 C8 123.99(10) . . ?
C2 C7 C8 117.82(10) . . ?
C9 C8 C7 120.59(10) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.65(10) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C9 118.60(10) . . ?
C1 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C20 C11 O3 119.79(9) . . ?
C20 C11 C12 121.47(10) . . ?
O3 C11 C12 118.73(9) . . ?
C13 C12 C11 120.63(10) . . ?
C13 C12 C17 119.67(9) . . ?
C11 C12 C17 119.69(9) . . ?
C14 C13 O4 119.72(10) . . ?
C14 C13 C12 121.39(10) . . ?
O4 C13 C12 118.88(9) . . ?
C13 C14 C15 118.85(10) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 121.52(10) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 120.47(10) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 118.07(10) . . ?
C12 C17 C18 118.09(10) . . ?
C16 C17 C18 123.83(10) . . ?
C19 C18 C17 120.35(10) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 121.67(10) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C11 C20 C19 118.72(10) . . ?
C11 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
O5 B1 O2 116.09(9) . . ?
O5 B1 O1 120.13(10) . . ?
O2 B1 O1 123.75(10) . . ?
O5 B2 O4 116.60(10) . . ?
O5 B2 O3 120.12(10) . . ?
O4 B2 O3 123.19(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_5a
_database_code_depnum_ccdc_archive 'CCDC 1962513'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_date             2019-04-30T12:44:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H9 B F2 O2'
_chemical_formula_weight         282.04

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.57980(10)
_cell_length_b                   11.10590(10)
_cell_length_c                   12.94850(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.9770(10)
_cell_angle_gamma                90
_cell_volume                     1215.16(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11979
_cell_measurement_theta_min      5.222
_cell_measurement_theta_max      77.049

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.101
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0513
-5 2 0 0.0786
0 0 8 0.0682
5 -2 -1 0.0902
0 -7 0 0.0627
-4 -4 0 0.0752
0 7 0 0.0432
0 6 5 0.0455
-2 -4 -5 0.0698
1 -6 -5 0.0604
0 -5 6 0.0509
0 5 -6 0.0463
1 -7 -2 0.0485
-4 -4 -2 0.0617


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.48a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.904

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0510771
_diffrn_orient_matrix_ub_12      0.1290691
_diffrn_orient_matrix_ub_13      -0.0222314
_diffrn_orient_matrix_ub_21      -0.0137732
_diffrn_orient_matrix_ub_22      -0.0310225
_diffrn_orient_matrix_ub_23      -0.1172176
_diffrn_orient_matrix_ub_31      -0.174411
_diffrn_orient_matrix_ub_32      0.0402946
_diffrn_orient_matrix_ub_33      -0.0191039
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_number            14851
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.234
_diffrn_reflns_theta_max         77.414
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             2543
_reflns_number_gt                2407
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.4446P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2543
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 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'

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 0.96353(8) 0.13924(6) 0.33085(5) 0.02513(17) Uani 1 1 d . . . . .
F2 F 0.73604(8) 0.49877(6) 0.18672(5) 0.02203(16) Uani 1 1 d . . . . .
O1 O 0.79938(8) 0.43620(7) 0.42247(6) 0.01668(17) Uani 1 1 d . . . . .
O2 O 0.65871(8) 0.25028(7) 0.38246(6) 0.01749(17) Uani 1 1 d . . . . .
C1 C 0.84518(12) 0.31944(9) 0.26301(8) 0.0167(2) Uani 1 1 d . . . . .
C2 C 0.94116(12) 0.22104(10) 0.25178(8) 0.0181(2) Uani 1 1 d . . . . .
C3 C 1.01691(12) 0.20265(10) 0.16732(9) 0.0198(2) Uani 1 1 d . . . . .
H3 H 1.081915 0.134062 0.163724 0.024 Uiso 1 1 calc R U . . .
C4 C 0.99455(12) 0.28824(10) 0.08770(8) 0.0199(2) Uani 1 1 d . . . . .
H4 H 1.045204 0.277942 0.028611 0.024 Uiso 1 1 calc R U . . .
C5 C 0.89947(12) 0.38850(10) 0.09305(8) 0.0194(2) Uani 1 1 d . . . . .
H5 H 0.883208 0.446453 0.03827 0.023 Uiso 1 1 calc R U . . .
C6 C 0.82935(12) 0.40102(9) 0.18086(8) 0.0171(2) Uani 1 1 d . . . . .
C7 C 0.73301(11) 0.45106(9) 0.51217(8) 0.0150(2) Uani 1 1 d . . . . .
C8 C 0.62394(11) 0.36377(9) 0.53507(8) 0.0148(2) Uani 1 1 d . . . . .
C9 C 0.58576(12) 0.26267(9) 0.46939(8) 0.0159(2) Uani 1 1 d . . . . .
C10 C 0.48121(12) 0.17720(10) 0.49023(8) 0.0185(2) Uani 1 1 d . . . . .
H10 H 0.456493 0.109774 0.445217 0.022 Uiso 1 1 calc R U . . .
C11 C 0.41037(12) 0.19132(10) 0.58050(9) 0.0198(2) Uani 1 1 d . . . . .
H11 H 0.336861 0.132654 0.595507 0.024 Uiso 1 1 calc R U . . .
C12 C 0.44532(12) 0.28759(10) 0.64677(8) 0.0188(2) Uani 1 1 d . . . . .
H12 H 0.396241 0.294566 0.706866 0.023 Uiso 1 1 calc R U . . .
C13 C 0.55438(12) 0.37697(9) 0.62622(8) 0.0164(2) Uani 1 1 d . . . . .
C14 C 0.59920(12) 0.47765(10) 0.69209(8) 0.0187(2) Uani 1 1 d . . . . .
H14 H 0.554044 0.488564 0.753442 0.022 Uiso 1 1 calc R U . . .
C15 C 0.70724(12) 0.55939(10) 0.66790(8) 0.0191(2) Uani 1 1 d . . . . .
H15 H 0.736567 0.625826 0.713332 0.023 Uiso 1 1 calc R U . . .
C16 C 0.77599(12) 0.54682(9) 0.57660(8) 0.0173(2) Uani 1 1 d . . . . .
H16 H 0.850608 0.604045 0.560608 0.021 Uiso 1 1 calc R U . . .
B1 B 0.76204(13) 0.33635(11) 0.36127(9) 0.0162(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.3573(12) . ?
F2 C6 1.3587(12) . ?
O1 B1 1.3683(14) . ?
O1 C7 1.3892(12) . ?
O2 B1 1.3636(14) . ?
O2 C9 1.3863(12) . ?
C1 C6 1.3859(15) . ?
C1 C2 1.3910(15) . ?
C1 B1 1.5740(15) . ?
C2 C3 1.3807(14) . ?
C3 C4 1.3909(16) . ?
C3 H3 0.95 . ?
C4 C5 1.3892(16) . ?
C4 H4 0.95 . ?
C5 C6 1.3825(15) . ?
C5 H5 0.95 . ?
C7 C16 1.3626(15) . ?
C7 C8 1.4140(14) . ?
C8 C9 1.4124(14) . ?
C8 C13 1.4194(14) . ?
C9 C10 1.3647(15) . ?
C10 C11 1.4165(15) . ?
C10 H10 0.95 . ?
C11 C12 1.3711(16) . ?
C11 H11 0.95 . ?
C12 C13 1.4205(15) . ?
C12 H12 0.95 . ?
C13 C14 1.4185(15) . ?
C14 C15 1.3719(15) . ?
C14 H14 0.95 . ?
C15 C16 1.4165(14) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C7 119.45(8) . . ?
B1 O2 C9 119.64(8) . . ?
C6 C1 C2 114.48(9) . . ?
C6 C1 B1 122.99(9) . . ?
C2 C1 B1 122.52(9) . . ?
F1 C2 C3 118.29(9) . . ?
F1 C2 C1 117.12(9) . . ?
C3 C2 C1 124.57(10) . . ?
C2 C3 C4 117.56(10) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 121.17(10) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 117.69(10) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
F2 C6 C5 118.09(9) . . ?
F2 C6 C1 117.37(9) . . ?
C5 C6 C1 124.53(10) . . ?
C16 C7 O1 119.87(9) . . ?
C16 C7 C8 121.70(9) . . ?
O1 C7 C8 118.42(9) . . ?
C9 C8 C7 120.77(9) . . ?
C9 C8 C13 119.71(9) . . ?
C7 C8 C13 119.50(9) . . ?
C10 C9 O2 119.75(9) . . ?
C10 C9 C8 121.72(9) . . ?
O2 C9 C8 118.53(9) . . ?
C9 C10 C11 118.48(10) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 121.61(10) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.49(10) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C8 118.17(9) . . ?
C14 C13 C12 123.84(10) . . ?
C8 C13 C12 117.98(9) . . ?
C15 C14 C13 120.52(9) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.39(10) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C7 C16 C15 118.70(9) . . ?
C7 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
O2 B1 O1 123.15(10) . . ?
O2 B1 C1 118.71(9) . . ?
O1 B1 C1 118.13(9) . . ?

