# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_zhaojh_1022
_audit_block_doi                 10.5517/ccdc.csd.cc254zq1
_database_code_depnum_ccdc_archive 'CCDC 2000793'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0OB00028K 2020
loop_
_audit_author_name
_audit_author_address
'jiahui zhao'
;lanzhou university
China
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_audit_creation_date             2019-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 B N O2'
_chemical_formula_sum            'C14 H18 B N O2'
_chemical_formula_weight         243.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3720(3)
_cell_length_b                   12.8487(4)
_cell_length_c                   21.0007(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2798.70(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2329
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7650
_cell_measurement_theta_min      8.0750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6308
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         4.210
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -41.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega  -28.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -58.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega   40.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   21.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega  -17.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -13.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega   88.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   48.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   36.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega   48.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
 12 omega  100.00  136.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega  102.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 63

#__ type_ start__ end____ width___ exp.time_
 14 omega   48.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
 15 omega   54.00  101.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
 16 omega  142.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0098954000
_diffrn_orient_matrix_UB_12      0.0411805000
_diffrn_orient_matrix_UB_13      -0.0687388000
_diffrn_orient_matrix_UB_21      0.1129913000
_diffrn_orient_matrix_UB_22      0.0708417000
_diffrn_orient_matrix_UB_23      0.0198248000
_diffrn_orient_matrix_UB_31      0.0959472000
_diffrn_orient_matrix_UB_32      -0.0874632000
_diffrn_orient_matrix_UB_33      -0.0162916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1963
_reflns_number_total             2414
_reflns_odcompleteness_completeness 96.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+0.3437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1471
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C10(0.6) C11(0.6) H11A(0.6) H11B(0.6) H11C(0.6) C12(0.6) H12A(0.6)
 H12B(0.6) H12C(0.6) C13(0.6) H13A(0.6) H13B(0.6) H13C(0.6) C14(0.6) H14A(0.6)
 H14B(0.6) H14C(0.6) C10'(0.4) C11'(0.4) H11D(0.4) H11E(0.4) H11F(0.4)
 C12'(0.4) H12D(0.4) H12E(0.4) H12F(0.4) C13'(0.4) H13D(0.4) H13E(0.4)
 H13F(0.4) C14'(0.4) H14D(0.4) H14E(0.4) H14F(0.4)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C11'(H11D,H11E,H11F), C12'(H12D,H12E,H12F), C13'(H13D,H13E,H13F),
 C14'(H14D,H14E,H14F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.06583(11) 0.80144(9) 0.13417(6) 0.0559(3) Uani 1 1 d . . . . .
O2 O 0.14375(13) 0.67495(10) 0.06959(7) 0.0714(4) Uani 1 1 d . . . . .
N1 N -0.39358(15) 0.46940(12) 0.18122(9) 0.0685(5) Uani 1 1 d . . . . .
H1 H -0.423213 0.408818 0.171779 0.082 Uiso 1 1 calc R . . . .
C1 C -0.44982(18) 0.53804(17) 0.22197(10) 0.0705(5) Uani 1 1 d . . . . .
H1A H -0.526616 0.526558 0.243721 0.085 Uiso 1 1 calc R . . . .
C2 C -0.37786(18) 0.62521(16) 0.22621(10) 0.0658(5) Uani 1 1 d . . . . .
H2 H -0.395639 0.683417 0.251024 0.079 Uiso 1 1 calc R . . . .
C3 C -0.26878(15) 0.61109(13) 0.18519(8) 0.0503(4) Uani 1 1 d . . . . .
C4 C -0.16144(15) 0.67155(12) 0.16935(7) 0.0486(4) Uani 1 1 d . . . . .
H4 H -0.151719 0.737102 0.187503 0.058 Uiso 1 1 calc R . . . .
C5 C -0.06937(14) 0.63538(12) 0.12707(7) 0.0467(4) Uani 1 1 d . . . . .
C6 C -0.08666(17) 0.53538(13) 0.10037(9) 0.0563(4) Uani 1 1 d . . . . .
H6 H -0.025434 0.510366 0.071863 0.068 Uiso 1 1 calc R . . . .
C7 C -0.19092(18) 0.47378(13) 0.11511(9) 0.0627(5) Uani 1 1 d . . . . .
H7 H -0.200249 0.408068 0.097123 0.075 Uiso 1 1 calc R . . . .
C8 C -0.28174(15) 0.51216(13) 0.15746(8) 0.0530(4) Uani 1 1 d . . . . .
C9 C 0.1843(2) 0.84335(17) 0.10699(11) 0.0755(6) Uani 1 1 d . . . . .
B1 B 0.04863(17) 0.70376(14) 0.10993(9) 0.0476(4) Uani 1 1 d . . . . .
C10 C 0.2472(5) 0.7540(4) 0.0772(2) 0.0606(11) Uani 0.6 1 d . . P A 1
C11 C 0.3483(4) 0.7134(3) 0.1242(2) 0.0918(12) Uani 0.6 1 d . . P A 1
H11A H 0.310449 0.707679 0.165812 0.138 Uiso 0.6 1 calc GR . P A 1
H11B H 0.419725 0.760793 0.125767 0.138 Uiso 0.6 1 calc GR . P A 1
H11C H 0.377899 0.646196 0.110607 0.138 Uiso 0.6 1 calc GR . P A 1
C12 C 0.3072(6) 0.7674(5) 0.0132(3) 0.1079(19) Uani 0.6 1 d . . P A 1
H12A H 0.346408 0.703177 0.000199 0.162 Uiso 0.6 1 calc GR . P A 1
H12B H 0.371630 0.820954 0.015191 0.162 Uiso 0.6 1 calc GR . P A 1
H12C H 0.242067 0.786810 -0.017078 0.162 Uiso 0.6 1 calc GR . P A 1
C13 C 0.2443(4) 0.9156(3) 0.1517(2) 0.0865(12) Uani 0.6 1 d . . P A 1
H13A H 0.186509 0.972388 0.159965 0.130 Uiso 0.6 1 calc GR . P A 1
H13B H 0.322903 0.941974 0.133728 0.130 Uiso 0.6 1 calc GR . P A 1
H13C H 0.262980 0.880019 0.190822 0.130 Uiso 0.6 1 calc GR . P A 1
C14 C 0.1203(4) 0.9210(3) 0.0513(2) 0.0958(13) Uani 0.6 1 d . . P A 1
H14A H 0.077700 0.879419 0.019672 0.144 Uiso 0.6 1 calc GR . P A 1
H14B H 0.187425 0.961062 0.031525 0.144 Uiso 0.6 1 calc GR . P A 1
H14C H 0.059009 0.967158 0.070717 0.144 Uiso 0.6 1 calc GR . P A 1
C10' C 0.2172(7) 0.7676(7) 0.0511(3) 0.0622(17) Uani 0.4 1 d . . P A 2
C11' C 0.3559(7) 0.7298(7) 0.0384(5) 0.098(3) Uani 0.4 1 d . . P A 2
H11D H 0.388637 0.695412 0.075599 0.148 Uiso 0.4 1 calc GR . P A 2
H11E H 0.409716 0.788339 0.028359 0.148 Uiso 0.4 1 calc GR . P A 2
H11F H 0.355796 0.682037 0.003194 0.148 Uiso 0.4 1 calc GR . P A 2
C12' C 0.1614(6) 0.8172(6) -0.0080(3) 0.093(2) Uani 0.4 1 d . . P A 2
H12D H 0.157116 0.766492 -0.041506 0.140 Uiso 0.4 1 calc GR . P A 2
H12E H 0.215244 0.874061 -0.021089 0.140 Uiso 0.4 1 calc GR . P A 2
H12F H 0.076274 0.842573 0.001056 0.140 Uiso 0.4 1 calc GR . P A 2
C13' C 0.2955(6) 0.8010(6) 0.1662(3) 0.097(2) Uani 0.4 1 d . . P A 2
H13D H 0.274677 0.833118 0.206206 0.146 Uiso 0.4 1 calc GR . P A 2
H13E H 0.381373 0.820222 0.153925 0.146 Uiso 0.4 1 calc GR . P A 2
H13F H 0.290340 0.726685 0.170538 0.146 Uiso 0.4 1 calc GR . P A 2
C14' C 0.2005(7) 0.9471(4) 0.1007(4) 0.0902(19) Uani 0.4 1 d . . P A 2
H14D H 0.130184 0.975590 0.076593 0.135 Uiso 0.4 1 calc GR . P A 2
H14E H 0.280128 0.960689 0.078848 0.135 Uiso 0.4 1 calc GR . P A 2
H14F H 0.202826 0.978859 0.142024 0.135 Uiso 0.4 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.458(2) . ?
O1 B1 1.366(2) . ?
O2 B1 1.352(2) . ?
O2 C10 1.487(5) . ?
O2 C10' 1.466(8) . ?
N1 H1 0.8600 . ?
N1 C1 1.360(3) . ?
N1 C8 1.377(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.349(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.433(3) . ?
C3 C4 1.398(2) . ?
C3 C8 1.405(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(2) . ?
C5 C6 1.413(2) . ?
C5 B1 1.549(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C9 C10 1.461(5) . ?
C9 C13 1.460(4) . ?
C9 C14 1.675(5) . ?
C9 C10' 1.563(9) . ?
C9 C13' 1.782(6) . ?
C9 C14' 1.351(6) . ?
C10 C11 1.532(6) . ?
C10 C12 1.491(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C10' C11' 1.542(9) . ?
C10' C12' 1.511(8) . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C14' H14D 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H14F 0.9600 . ?

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 C9 107.67(14) . . ?
B1 O2 C10 105.8(2) . . ?
B1 O2 C10' 108.9(3) . . ?
C1 N1 H1 125.4 . . ?
C1 N1 C8 109.29(15) . . ?
C8 N1 H1 125.4 . . ?
N1 C1 H1A 125.0 . . ?
C2 C1 N1 110.04(17) . . ?
C2 C1 H1A 125.0 . . ?
C1 C2 H2 126.5 . . ?
C1 C2 C3 106.98(18) . . ?
C3 C2 H2 126.5 . . ?
C4 C3 C2 134.54(16) . . ?
C4 C3 C8 118.72(15) . . ?
C8 C3 C2 106.74(15) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.04(14) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.17(15) . . ?
C4 C5 B1 120.25(14) . . ?
C6 C5 B1 121.58(15) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.25(16) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 120.9 . . ?
C6 C7 C8 118.29(16) . . ?
C8 C7 H7 120.9 . . ?
N1 C8 C3 106.94(16) . . ?
N1 C8 C7 131.53(16) . . ?
C7 C8 C3 121.53(15) . . ?
O1 C9 C10 104.7(2) . . ?
O1 C9 C13 110.0(2) . . ?
O1 C9 C14 99.2(2) . . ?
O1 C9 C10' 104.4(3) . . ?
O1 C9 C13' 99.2(2) . . ?
C10 C9 C14 110.2(3) . . ?
C13 C9 C10 125.8(3) . . ?
C13 C9 C14 103.8(3) . . ?
C10' C9 C13' 101.1(4) . . ?
C14' C9 O1 120.5(3) . . ?
C14' C9 C10' 120.9(4) . . ?
C14' C9 C13' 106.9(5) . . ?
O1 B1 C5 122.53(15) . . ?
O2 B1 O1 112.94(15) . . ?
O2 B1 C5 124.53(16) . . ?
O2 C10 C11 109.3(3) . . ?
O2 C10 C12 106.5(4) . . ?
C9 C10 O2 105.1(3) . . ?
C9 C10 C11 107.3(4) . . ?
C9 C10 C12 118.8(4) . . ?
C12 C10 C11 109.6(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C10' C9 101.1(4) . . ?
O2 C10' C11' 106.0(6) . . ?
O2 C10' C12' 111.2(6) . . ?
C11' C10' C9 122.0(7) . . ?
C12' C10' C9 105.7(6) . . ?
C12' C10' C11' 110.4(6) . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C10' C12' H12D 109.5 . . ?
C10' C12' H12E 109.5 . . ?
C10' C12' H12F 109.5 . . ?
H12D C12' H12E 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C9 C13' H13D 109.5 . . ?
C9 C13' H13E 109.5 . . ?
C9 C13' H13F 109.5 . . ?
H13D C13' H13E 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C9 C14' H14D 109.5 . . ?
C9 C14' H14E 109.5 . . ?
C9 C14' H14F 109.5 . . ?
H14D C14' H14E 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C9 C10 O2 18.6(3) . . . . ?
O1 C9 C10 C11 -97.6(3) . . . . ?
O1 C9 C10 C12 137.5(4) . . . . ?
O1 C9 C10' O2 -20.6(4) . . . . ?
O1 C9 C10' C11' -137.6(6) . . . . ?
O1 C9 C10' C12' 95.4(5) . . . . ?
N1 C1 C2 C3 0.2(3) . . . . ?
C1 N1 C8 C3 0.3(2) . . . . ?
C1 N1 C8 C7 179.7(2) . . . . ?
C1 C2 C3 C4 -179.6(2) . . . . ?
C1 C2 C3 C8 0.0(2) . . . . ?
C2 C3 C4 C5 179.75(19) . . . . ?
C2 C3 C8 N1 -0.2(2) . . . . ?
C2 C3 C8 C7 -179.67(17) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C3 C4 C5 B1 179.76(15) . . . . ?
C4 C3 C8 N1 179.51(15) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 B1 O1 -1.3(3) . . . . ?
C4 C5 B1 O2 179.53(16) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C5 B1 O1 178.63(16) . . . . ?
C6 C5 B1 O2 -0.6(3) . . . . ?
C6 C7 C8 N1 -179.57(18) . . . . ?
C6 C7 C8 C3 -0.2(3) . . . . ?
C8 N1 C1 C2 -0.3(3) . . . . ?
C8 C3 C4 C5 0.2(2) . . . . ?
C9 O1 B1 O2 0.5(2) . . . . ?
C9 O1 B1 C5 -178.78(17) . . . . ?
B1 O1 C9 C10 -12.4(3) . . . . ?
B1 O1 C9 C13 -150.1(3) . . . . ?
B1 O1 C9 C14 101.5(2) . . . . ?
B1 O1 C9 C10' 13.1(3) . . . . ?
B1 O1 C9 C13' -91.0(3) . . . . ?
B1 O1 C9 C14' 153.2(5) . . . . ?
B1 O2 C10 C9 -18.6(3) . . . . ?
B1 O2 C10 C11 96.2(3) . . . . ?
B1 O2 C10 C12 -145.5(4) . . . . ?
B1 O2 C10' C9 21.6(4) . . . . ?
B1 O2 C10' C11' 149.9(5) . . . . ?
B1 O2 C10' C12' -90.2(6) . . . . ?
B1 C5 C6 C7 -179.98(17) . . . . ?
C10 O2 B1 O1 11.5(3) . . . . ?
C10 O2 B1 C5 -169.3(2) . . . . ?
C13 C9 C10 O2 147.3(3) . . . . ?
C13 C9 C10 C11 31.1(5) . . . . ?
C13 C9 C10 C12 -93.8(6) . . . . ?
C14 C9 C10 O2 -87.2(3) . . . . ?
C14 C9 C10 C11 156.6(3) . . . . ?
C14 C9 C10 C12 31.7(6) . . . . ?
C10' O2 B1 O1 -15.2(3) . . . . ?
C10' O2 B1 C5 164.1(3) . . . . ?
C13' C9 C10' O2 82.0(4) . . . . ?
C13' C9 C10' C11' -35.0(7) . . . . ?
C13' C9 C10' C12' -162.1(5) . . . . ?
C14' C9 C10' O2 -160.5(5) . . . . ?
C14' C9 C10' C11' 82.5(8) . . . . ?
C14' C9 C10' C12' -44.5(7) . . . . ?

_olex2_date_sample_data_collection 2019-10-23
_olex2_submission_special_instructions 'No special instructions were received'
