# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_appiariusy190905_0m
_database_code_depnum_ccdc_archive 'CCDC 1998251'
loop_
_audit_author_name
_audit_author_address
'Enno Lork'
;University of Bremen
Germany
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-08-14 downloaded from the CCDC.
;
_audit_creation_date             2019-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yappiarius@uni-bremen.de
e.lork@uni-bremen.de
staubitz@uni-bremen.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H34 B2 N2'
_chemical_formula_sum            'C36 H34 B2 N2'
_chemical_formula_weight         516.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.0449(16)
_cell_length_b                   7.163(3)
_cell_length_c                   16.726(5)
_cell_angle_alpha                91.335(15)
_cell_angle_beta                 100.001(12)
_cell_angle_gamma                104.386(14)
_cell_volume                     689.2(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5669
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0891 before and 0.0595 after correction. The Ratio of minimum to maximum transmission is 0.9572. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19599
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.479
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2229
_reflns_number_total             3325
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.4485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1434
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C12A(H12A)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N1 N 0.3242(3) 0.6357(2) 0.32656(8) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.2903(3) 0.4949(2) 0.38169(10) 0.0152(4) Uani 1 1 d . . . . .
C2 C 0.1445(3) 0.5018(2) 0.44097(10) 0.0149(4) Uani 1 1 d . . . . .
C3 C 0.0319(3) 0.6479(2) 0.44780(10) 0.0164(4) Uani 1 1 d . . . . .
H3 H 0.053729 0.749846 0.412330 0.020 Uiso 1 1 calc R . . . .
C4 C -0.1115(3) 0.6503(2) 0.50458(10) 0.0154(4) Uani 1 1 d . . . . .
C5 C 0.2293(3) 0.1992(2) 0.49128(10) 0.0170(4) Uani 1 1 d . . . . .
H5 H 0.210880 0.099857 0.528060 0.020 Uiso 1 1 calc R . . . .
C6 C 0.3657(3) 0.1982(2) 0.43559(10) 0.0180(4) Uani 1 1 d . . . . .
H6 H 0.441896 0.097470 0.433873 0.022 Uiso 1 1 calc R . . . .
C7 C 0.3990(3) 0.3455(2) 0.37876(10) 0.0161(4) Uani 1 1 d . . . . .
C8 C 0.5400(3) 0.3389(3) 0.31896(11) 0.0204(4) Uani 1 1 d . . . . .
H8 H 0.611268 0.235011 0.317433 0.025 Uiso 1 1 calc R . . . .
C9 C 0.5760(3) 0.4752(3) 0.26421(11) 0.0210(4) Uani 1 1 d . . . . .
H9 H 0.673355 0.467337 0.226030 0.025 Uiso 1 1 calc R . . . .
C10 C 0.4695(3) 0.8051(2) 0.20283(10) 0.0158(4) Uani 1 1 d . . . . .
C11 C 0.6733(3) 0.9544(2) 0.20475(10) 0.0170(4) Uani 1 1 d . . . . .
C11A C 0.2732(3) 0.8068(3) 0.14365(11) 0.0205(4) Uani 1 1 d . . . . .
C12 C 0.6757(3) 1.1002(2) 0.15086(10) 0.0192(4) Uani 1 1 d . . . . .
H12 H 0.816204 1.196709 0.151790 0.023 Uiso 1 1 calc R . . . .
C12A C 0.2796(3) 0.9586(3) 0.09277(11) 0.0238(4) Uani 1 1 d . . . . .
H12A H 0.143533 0.959859 0.054773 0.029 Uiso 1 1 calc R . . . .
C13 C 0.4781(3) 1.1080(3) 0.09578(11) 0.0220(4) Uani 1 1 d . . . . .
C14 C 0.4771(4) 1.2739(3) 0.04212(12) 0.0316(5) Uani 1 1 d . . . . .
H14A H 0.415321 1.369711 0.067550 0.047 Uiso 1 1 calc GR . . . .
H14B H 0.379148 1.225914 -0.011022 0.047 Uiso 1 1 calc GR . . . .
H14C H 0.636053 1.333879 0.034906 0.047 Uiso 1 1 calc GR . . . .
C15 C 0.8904(3) 0.9627(3) 0.26688(11) 0.0234(4) Uani 1 1 d . . . . .
H15A H 0.879116 1.024245 0.318443 0.035 Uiso 1 1 calc GR . . . .
H15B H 1.026563 1.037841 0.247067 0.035 Uiso 1 1 calc GR . . . .
H15C H 0.905957 0.831289 0.275374 0.035 Uiso 1 1 calc GR . . . .
C15A C 0.0565(3) 0.6408(3) 0.13091(12) 0.0283(5) Uani 1 1 d . . . . .
H15D H 0.049506 0.561435 0.081551 0.042 Uiso 1 1 calc GR . . . .
H15E H -0.081115 0.691859 0.125090 0.042 Uiso 1 1 calc GR . . . .
H15F H 0.060912 0.561526 0.177859 0.042 Uiso 1 1 calc GR . . . .
B1 B 0.4600(3) 0.6402(3) 0.26443(12) 0.0170(4) Uani 1 1 d . . . . .
H1 H 0.250(4) 0.729(3) 0.3296(12) 0.024(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.384(2) . ?
N1 B1 1.428(2) . ?
N1 H1 0.89(2) . ?
C1 C2 1.444(2) . ?
C1 C7 1.392(2) . ?
C2 C3 1.395(2) . ?
C2 C4 1.435(2) 2_566 ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C4 C5 1.438(2) 2_566 ?
C5 H5 0.9500 . ?
C5 C6 1.348(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.436(2) . ?
C7 C8 1.429(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.358(2) . ?
C9 H9 0.9500 . ?
C9 B1 1.517(3) . ?
C10 C11 1.412(2) . ?
C10 C11A 1.410(2) . ?
C10 B1 1.582(2) . ?
C11 C12 1.394(2) . ?
C11 C15 1.513(2) . ?
C11A C12A 1.393(2) . ?
C11A C15A 1.514(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(3) . ?
C12A H12A 0.9500 . ?
C12A C13 1.388(3) . ?
C13 C14 1.506(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 B1 125.40(15) . . ?
C1 N1 H1 116.4(13) . . ?
B1 N1 H1 118.1(13) . . ?
N1 C1 C2 120.86(15) . . ?
N1 C1 C7 118.69(15) . . ?
C7 C1 C2 120.45(15) . . ?
C3 C2 C1 123.53(15) . . ?
C3 C2 C4 118.02(15) . 2_566 ?
C4 C2 C1 118.44(15) 2_566 . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.71(15) . . ?
C4 C3 H3 118.6 . . ?
C2 C4 C5 119.45(15) 2_566 2_566 ?
C3 C4 C2 119.27(15) . 2_566 ?
C3 C4 C5 121.27(15) . 2_566 ?
C4 C5 H5 119.8 2_566 . ?
C6 C5 C4 120.49(15) . 2_566 ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.76(16) . . ?
C7 C6 H6 119.1 . . ?
C1 C7 C6 119.38(15) . . ?
C1 C7 C8 119.83(15) . . ?
C8 C7 C6 120.79(16) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 C7 122.64(16) . . ?
C9 C8 H8 118.7 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 B1 119.58(16) . . ?
B1 C9 H9 120.2 . . ?
C11 C10 B1 121.56(15) . . ?
C11A C10 C11 117.72(15) . . ?
C11A C10 B1 120.72(15) . . ?
C10 C11 C15 120.71(15) . . ?
C12 C11 C10 120.41(16) . . ?
C12 C11 C15 118.85(16) . . ?
C10 C11A C15A 121.24(16) . . ?
C12A C11A C10 120.18(16) . . ?
C12A C11A C15A 118.51(16) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.77(16) . . ?
C13 C12 H12 119.1 . . ?
C11A C12A H12A 118.9 . . ?
C13 C12A C11A 122.15(17) . . ?
C13 C12A H12A 118.9 . . ?
C12 C13 C14 121.48(17) . . ?
C12A C13 C12 117.59(16) . . ?
C12A C13 C14 120.92(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11A C15A H15D 109.5 . . ?
C11A C15A H15E 109.5 . . ?
C11A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
N1 B1 C9 113.84(16) . . ?
N1 B1 C10 119.17(16) . . ?
C9 B1 C10 126.96(16) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_appiariusy190913_0ma
_database_code_depnum_ccdc_archive 'CCDC 1998253'
loop_
_audit_author_name
_audit_author_address
'Enno Lork'
;University of Bremen
Germany
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-08-14 downloaded from the CCDC.
;
_audit_creation_date             2019-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yappiarius@uni-bremen.de
e.lork@uni-bremen.de
staubitz@uni-bremen.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 B N'
_chemical_formula_sum            'C21 H20 B N'
_chemical_formula_weight         297.19
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5758(3)
_cell_length_b                   7.1933(3)
_cell_length_c                   15.4440(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.3710(10)
_cell_angle_gamma                90
_cell_volume                     836.42(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      33.14
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0714 before and 0.0436 after correction. The Ratio of minimum to maximum transmission is 0.9586. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.255
_diffrn_reflns_theta_min         2.654
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5472
_reflns_number_total             6419
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2253 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         6419
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0801P)²+0.0447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C15(H15),
 C15A(H15A)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N1 N 0.65639(15) 0.41387(17) 0.34038(7) 0.0165(2) Uani 1 1 d . . . . .
C1 C 0.75373(17) 0.34462(19) 0.41415(9) 0.0155(2) Uani 1 1 d . . . . .
C2 C 0.68453(18) 0.34426(19) 0.49685(9) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.51036(19) 0.4043(2) 0.50835(10) 0.0184(3) Uani 1 1 d . . . . .
H3 H 0.434050 0.446781 0.459380 0.022 Uiso 1 1 calc R . . . .
C4 C 0.4499(2) 0.4023(2) 0.58898(10) 0.0220(3) Uani 1 1 d . . . . .
H4 H 0.332778 0.443142 0.595226 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5608(2) 0.3399(2) 0.66237(10) 0.0240(3) Uani 1 1 d . . . . .
H5 H 0.518671 0.339289 0.718062 0.029 Uiso 1 1 calc R . . . .
C6 C 0.7300(2) 0.2799(2) 0.65346(9) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.803591 0.236853 0.703231 0.027 Uiso 1 1 calc R . . . .
C7 C 0.79637(19) 0.28113(19) 0.57135(9) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.9726(2) 0.2208(2) 0.56225(10) 0.0222(3) Uani 1 1 d . . . . .
H8 H 1.048433 0.182644 0.612199 0.027 Uiso 1 1 calc R . . . .
C9 C 1.03252(18) 0.2176(2) 0.48281(10) 0.0221(3) Uani 1 1 d . . . . .
H9 H 1.149531 0.174410 0.477954 0.026 Uiso 1 1 calc R . . . .
C10 C 0.92497(18) 0.2770(2) 0.40648(9) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.99205(19) 0.2748(3) 0.32356(10) 0.0249(3) Uani 1 1 d . . . . .
H11 H 1.106818 0.224280 0.319830 0.030 Uiso 1 1 calc R . . . .
C12 C 0.8990(2) 0.3417(3) 0.24982(10) 0.0261(3) Uani 1 1 d . . . . .
H12 H 0.948460 0.339147 0.195918 0.031 Uiso 1 1 calc R . . . .
C13 C 0.58156(18) 0.5100(2) 0.18032(9) 0.0187(3) Uani 1 1 d . . . . .
C14 C 0.6193(2) 0.6813(2) 0.14213(9) 0.0218(3) Uani 1 1 d . . . . .
C14A C 0.41772(18) 0.4234(2) 0.15280(9) 0.0196(3) Uani 1 1 d . . . . .
C15 C 0.4932(2) 0.7648(2) 0.08171(9) 0.0242(3) Uani 1 1 d . . . . .
H15 H 0.520805 0.879598 0.055984 0.029 Uiso 1 1 calc R . . . .
C15A C 0.2938(2) 0.5121(2) 0.09324(9) 0.0231(3) Uani 1 1 d . . . . .
H15A H 0.183049 0.453387 0.076195 0.028 Uiso 1 1 calc R . . . .
C16 C 0.3285(2) 0.6843(3) 0.05828(9) 0.0253(3) Uani 1 1 d . . . . .
C17 C 0.1911(3) 0.7810(4) -0.00429(12) 0.0397(5) Uani 1 1 d . . . . .
H17A H 0.103185 0.690196 -0.029046 0.060 Uiso 1 1 calc GR . . . .
H17B H 0.249205 0.838342 -0.051247 0.060 Uiso 1 1 calc GR . . . .
H17C H 0.131778 0.877307 0.026806 0.060 Uiso 1 1 calc GR . . . .
C18 C 0.7939(2) 0.7786(3) 0.16772(12) 0.0337(4) Uani 1 1 d . . . . .
H18A H 0.802044 0.888725 0.131052 0.051 Uiso 1 1 calc GR . . . .
H18B H 0.892003 0.693752 0.159768 0.051 Uiso 1 1 calc GR . . . .
H18C H 0.800841 0.816369 0.228973 0.051 Uiso 1 1 calc GR . . . .
C18A C 0.3764(2) 0.2314(2) 0.18466(11) 0.0276(3) Uani 1 1 d . . . . .
H18D H 0.260385 0.191147 0.156494 0.041 Uiso 1 1 calc GR . . . .
H18E H 0.373895 0.234206 0.247956 0.041 Uiso 1 1 calc GR . . . .
H18F H 0.468086 0.144151 0.170200 0.041 Uiso 1 1 calc GR . . . .
B1 B 0.7138(2) 0.4211(2) 0.25520(10) 0.0193(3) Uani 1 1 d . . . . .
H1 H 0.554(3) 0.459(3) 0.3480(12) 0.020(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3797(16) . ?
N1 B1 1.4317(19) . ?
N1 H1 0.86(2) . ?
C1 C2 1.4333(17) . ?
C1 C10 1.4027(18) . ?
C2 C3 1.4182(19) . ?
C2 C7 1.4253(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.407(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.415(2) . ?
C7 C8 1.425(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.355(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.4224(19) . ?
C10 C11 1.429(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.359(2) . ?
C12 H12 0.9500 . ?
C12 B1 1.526(2) . ?
C13 C14 1.409(2) . ?
C13 C14A 1.411(2) . ?
C13 B1 1.579(2) . ?
C14 C15 1.395(2) . ?
C14 C18 1.509(2) . ?
C14A C15A 1.3939(19) . ?
C14A C18A 1.511(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C15A H15A 0.9500 . ?
C15A C16 1.388(2) . ?
C16 C17 1.509(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 B1 125.65(11) . . ?
C1 N1 H1 115.5(13) . . ?
B1 N1 H1 118.8(13) . . ?
N1 C1 C2 121.44(11) . . ?
N1 C1 C10 118.03(12) . . ?
C10 C1 C2 120.52(11) . . ?
C3 C2 C1 123.26(11) . . ?
C3 C2 C7 118.29(12) . . ?
C7 C2 C1 118.45(11) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.24(13) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.29(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.98(13) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.07(13) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 119.13(12) . . ?
C6 C7 C8 121.09(12) . . ?
C8 C7 C2 119.78(12) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.42(12) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.77(13) . . ?
C10 C9 H9 119.1 . . ?
C1 C10 C9 118.97(12) . . ?
C1 C10 C11 120.25(12) . . ?
C9 C10 C11 120.75(12) . . ?
C10 C11 H11 118.5 . . ?
C12 C11 C10 122.96(13) . . ?
C12 C11 H11 118.5 . . ?
C11 C12 H12 120.6 . . ?
C11 C12 B1 118.77(13) . . ?
B1 C12 H12 120.6 . . ?
C14 C13 C14A 118.20(13) . . ?
C14 C13 B1 121.26(13) . . ?
C14A C13 B1 120.47(13) . . ?
C13 C14 C18 120.57(14) . . ?
C15 C14 C13 120.02(14) . . ?
C15 C14 C18 119.39(14) . . ?
C13 C14A C18A 120.83(13) . . ?
C15A C14A C13 120.14(14) . . ?
C15A C14A C18A 118.99(13) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.65(14) . . ?
C16 C15 H15 119.2 . . ?
C14A C15A H15A 119.3 . . ?
C16 C15A C14A 121.48(14) . . ?
C16 C15A H15A 119.3 . . ?
C15 C16 C15A 118.36(14) . . ?
C15 C16 C17 120.76(16) . . ?
C15A C16 C17 120.88(16) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14A C18A H18D 109.5 . . ?
C14A C18A H18E 109.5 . . ?
C14A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N1 B1 C12 114.31(13) . . ?
N1 B1 C13 117.05(12) . . ?
C12 B1 C13 128.64(13) . . ?

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
N1 C1 C2 C3 3.5(2) . . . . ?
N1 C1 C2 C7 -176.22(12) . . . . ?
N1 C1 C10 C9 175.47(14) . . . . ?
N1 C1 C10 C11 -2.2(2) . . . . ?
C1 N1 B1 C12 0.5(2) . . . . ?
C1 N1 B1 C13 -178.85(13) . . . . ?
C1 C2 C3 C4 -179.72(14) . . . . ?
C1 C2 C7 C6 -179.98(13) . . . . ?
C1 C2 C7 C8 0.1(2) . . . . ?
C1 C10 C11 C12 2.2(3) . . . . ?
C2 C1 C10 C9 -3.4(2) . . . . ?
C2 C1 C10 C11 178.92(15) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C2 C7 C8 C9 -2.1(2) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C3 C2 C7 C8 -179.63(13) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C2 -0.6(2) . . . . ?
C5 C6 C7 C8 179.30(15) . . . . ?
C6 C7 C8 C9 178.03(15) . . . . ?
C7 C2 C3 C4 0.0(2) . . . . ?
C7 C8 C9 C10 1.3(2) . . . . ?
C8 C9 C10 C1 1.4(2) . . . . ?
C8 C9 C10 C11 179.10(15) . . . . ?
C9 C10 C11 C12 -175.46(16) . . . . ?
C10 C1 C2 C3 -177.65(14) . . . . ?
C10 C1 C2 C7 2.6(2) . . . . ?
C10 C11 C12 B1 -0.7(3) . . . . ?
C11 C12 B1 N1 -0.6(2) . . . . ?
C11 C12 B1 C13 178.67(17) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C13 C14A C15A C16 1.3(2) . . . . ?
C14 C13 C14A C15A -3.7(2) . . . . ?
C14 C13 C14A C18A 174.09(13) . . . . ?
C14 C13 B1 N1 111.33(16) . . . . ?
C14 C13 B1 C12 -68.0(2) . . . . ?
C14 C15 C16 C15A -3.1(2) . . . . ?
C14 C15 C16 C17 177.36(15) . . . . ?
C14A C13 C14 C15 2.8(2) . . . . ?
C14A C13 C14 C18 -178.83(15) . . . . ?
C14A C13 B1 N1 -65.63(19) . . . . ?
C14A C13 B1 C12 115.07(19) . . . . ?
C14A C15A C16 C15 2.2(2) . . . . ?
C14A C15A C16 C17 -178.34(15) . . . . ?
C18 C14 C15 C16 -177.74(15) . . . . ?
C18A C14A C15A C16 -176.57(14) . . . . ?
B1 N1 C1 C2 179.73(13) . . . . ?
B1 N1 C1 C10 0.9(2) . . . . ?
B1 C13 C14 C15 -174.25(13) . . . . ?
B1 C13 C14 C18 4.1(2) . . . . ?
B1 C13 C14A C15A 173.32(13) . . . . ?
B1 C13 C14A C18A -8.9(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_appiariusy190906_0m
_database_code_depnum_ccdc_archive 'CCDC 1998252'
loop_
_audit_author_name
_audit_author_address
'Enno Lork'
;University of Bremen
Germany
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-08-14 downloaded from the CCDC.
;
_audit_creation_date             2019-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yappiarius@uni-bremen.de
e.lork@uni-bremen.de
staubitz@uni-bremen.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 B N S'
_chemical_formula_sum            'C19 H18 B N S'
_chemical_formula_weight         303.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0030(3)
_cell_length_b                   8.2368(3)
_cell_length_c                   12.5344(5)
_cell_angle_alpha                97.8090(10)
_cell_angle_beta                 97.8300(10)
_cell_angle_gamma                100.0790(10)
_cell_volume                     795.04(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9321
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      33.15
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0941 before and 0.0438 after correction. The Ratio of minimum to maximum transmission is 0.9423. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.227
_diffrn_reflns_theta_min         2.546
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5256
_reflns_number_total             6092
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         6092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.2491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13A(H13A), C9(H9), C7(H7), C6(H6), C4(H4), C13(H13), C10(H10), C3(H3)
2.b Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C16(H16D,H16E,H16F), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
S1 S 0.55776(3) 0.28918(3) 0.50984(2) 0.01986(7) Uani 1 1 d . . . . .
N1 N 0.68037(10) 0.47484(9) 0.31840(6) 0.01418(13) Uani 1 1 d . . . . .
C1 C 0.79157(11) 0.38993(10) 0.37171(7) 0.01301(14) Uani 1 1 d . . . . .
C2 C 0.74808(11) 0.30351(10) 0.45668(7) 0.01433(15) Uani 1 1 d . . . . .
C8 C 0.95441(11) 0.38940(10) 0.34122(7) 0.01423(15) Uani 1 1 d . . . . .
C11 C 0.57441(11) 0.65036(10) 0.17599(7) 0.01352(14) Uani 1 1 d . . . . .
C14 C 0.31808(12) 0.80701(12) 0.07807(7) 0.01759(16) Uani 1 1 d . . . . .
C13A C 0.28884(11) 0.63433(11) 0.07446(7) 0.01622(15) Uani 1 1 d . . . . .
H13A H 0.181122 0.568732 0.038610 0.019 Uiso 1 1 calc R . . . .
C9 C 1.00262(11) 0.47918(11) 0.25592(7) 0.01689(16) Uani 1 1 d . . . . .
H9 H 1.113440 0.479840 0.236590 0.020 Uiso 1 1 calc R . . . .
C12A C 0.41351(11) 0.55518(10) 0.12209(7) 0.01388(14) Uani 1 1 d . . . . .
C7 C 1.06839(11) 0.30240(11) 0.39647(8) 0.01685(16) Uani 1 1 d . . . . .
H7 H 1.178184 0.302570 0.375631 0.020 Uiso 1 1 calc R . . . .
C12 C 0.60536(11) 0.82504(11) 0.17797(7) 0.01502(15) Uani 1 1 d . . . . .
C6 C 1.02490(12) 0.21812(11) 0.47900(7) 0.01729(16) Uani 1 1 d . . . . .
H6 H 1.103561 0.160875 0.514625 0.021 Uiso 1 1 calc R . . . .
C4 C 0.78876(13) 0.14022(12) 0.59406(8) 0.01965(17) Uani 1 1 d . . . . .
H4 H 0.846678 0.076325 0.638896 0.024 Uiso 1 1 calc R . . . .
C13 C 0.47788(12) 0.90059(11) 0.12945(7) 0.01707(16) Uani 1 1 d . . . . .
H13 H 0.500714 1.018214 0.131560 0.020 Uiso 1 1 calc R . . . .
C5 C 0.86170(12) 0.21738(11) 0.51047(7) 0.01539(15) Uani 1 1 d . . . . .
C10 C 0.89551(12) 0.56327(11) 0.20180(7) 0.01699(16) Uani 1 1 d . . . . .
H10 H 0.931758 0.621337 0.145866 0.020 Uiso 1 1 calc R . . . .
C16A C 0.37403(12) 0.36674(11) 0.11105(8) 0.01792(16) Uani 1 1 d . . . . .
H16A H 0.470458 0.321655 0.086681 0.027 Uiso 1 1 calc GR . . . .
H16B H 0.269440 0.321538 0.057446 0.027 Uiso 1 1 calc GR . . . .
H16C H 0.356613 0.334883 0.181867 0.027 Uiso 1 1 calc GR . . . .
C3 C 0.62897(14) 0.16794(13) 0.60235(8) 0.02286(19) Uani 1 1 d . . . . .
H3 H 0.562824 0.125414 0.653499 0.027 Uiso 1 1 calc R . . . .
C16 C 0.77370(13) 0.93447(12) 0.23547(8) 0.02151(18) Uani 1 1 d . . . . .
H16D H 0.791672 0.920855 0.312406 0.032 Uiso 1 1 calc GR . . . .
H16E H 0.770455 1.051610 0.230455 0.032 Uiso 1 1 calc GR . . . .
H16F H 0.868194 0.901957 0.200876 0.032 Uiso 1 1 calc GR . . . .
C15 C 0.17966(14) 0.88939(14) 0.02787(10) 0.0268(2) Uani 1 1 d . . . . .
H15A H 0.110983 0.814066 -0.036419 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.232862 0.993589 0.006044 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.105147 0.914056 0.081339 0.040 Uiso 1 1 calc GR . . . .
B1 B 0.71661(12) 0.56382(12) 0.23148(8) 0.01429(16) Uani 1 1 d . . . . .
H1 H 0.583(2) 0.4737(19) 0.3432(12) 0.030(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.7358(9) . ?
S1 C3 1.7322(10) . ?
N1 C1 1.3822(10) . ?
N1 B1 1.4273(12) . ?
N1 H1 0.878(16) . ?
C1 C2 1.4079(12) . ?
C1 C8 1.4078(12) . ?
C2 C5 1.4048(11) . ?
C8 C9 1.4375(12) . ?
C8 C7 1.4201(12) . ?
C11 C12A 1.4124(12) . ?
C11 C12 1.4128(12) . ?
C11 B1 1.5779(12) . ?
C14 C13A 1.3939(13) . ?
C14 C13 1.3929(13) . ?
C14 C15 1.5076(13) . ?
C13A H13A 0.9500 . ?
C13A C12A 1.3957(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.3608(12) . ?
C12A C16A 1.5121(12) . ?
C7 H7 0.9500 . ?
C7 C6 1.3718(13) . ?
C12 C13 1.3978(12) . ?
C12 C16 1.5102(13) . ?
C6 H6 0.9500 . ?
C6 C5 1.4141(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.4353(13) . ?
C4 C3 1.3529(14) . ?
C13 H13 0.9500 . ?
C10 H10 0.9500 . ?
C10 B1 1.5281(13) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C3 H3 0.9500 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C2 91.26(4) . . ?
C1 N1 B1 124.79(7) . . ?
C1 N1 H1 114.9(10) . . ?
B1 N1 H1 120.3(10) . . ?
N1 C1 C2 122.18(8) . . ?
N1 C1 C8 119.54(8) . . ?
C8 C1 C2 118.28(7) . . ?
C1 C2 S1 126.71(6) . . ?
C5 C2 S1 111.40(6) . . ?
C5 C2 C1 121.88(8) . . ?
C1 C8 C9 119.21(7) . . ?
C1 C8 C7 119.32(8) . . ?
C7 C8 C9 121.46(8) . . ?
C12A C11 C12 118.22(7) . . ?
C12A C11 B1 120.93(7) . . ?
C12 C11 B1 120.84(8) . . ?
C13A C14 C15 120.60(9) . . ?
C13 C14 C13A 118.19(8) . . ?
C13 C14 C15 121.21(9) . . ?
C14 C13A H13A 119.1 . . ?
C14 C13A C12A 121.79(8) . . ?
C12A C13A H13A 119.1 . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.48(8) . . ?
C10 C9 H9 118.8 . . ?
C11 C12A C16A 121.42(7) . . ?
C13A C12A C11 120.04(8) . . ?
C13A C12A C16A 118.51(8) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 C8 122.05(8) . . ?
C6 C7 H7 119.0 . . ?
C11 C12 C16 120.95(8) . . ?
C13 C12 C11 120.36(8) . . ?
C13 C12 C16 118.65(8) . . ?
C7 C6 H6 120.4 . . ?
C7 C6 C5 119.28(8) . . ?
C5 C6 H6 120.4 . . ?
C5 C4 H4 123.5 . . ?
C3 C4 H4 123.5 . . ?
C3 C4 C5 113.00(8) . . ?
C14 C13 C12 121.37(8) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C2 C5 C6 119.19(8) . . ?
C2 C5 C4 111.48(8) . . ?
C6 C5 C4 129.33(8) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 B1 119.66(8) . . ?
B1 C10 H10 120.2 . . ?
C12A C16A H16A 109.5 . . ?
C12A C16A H16B 109.5 . . ?
C12A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
S1 C3 H3 123.6 . . ?
C4 C3 S1 112.86(7) . . ?
C4 C3 H3 123.6 . . ?
C12 C16 H16D 109.5 . . ?
C12 C16 H16E 109.5 . . ?
C12 C16 H16F 109.5 . . ?
H16D C16 H16E 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 B1 C11 119.04(8) . . ?
N1 B1 C10 114.29(7) . . ?
C10 B1 C11 126.66(8) . . ?

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
S1 C2 C5 C6 -178.92(7) . . . . ?
S1 C2 C5 C4 0.41(10) . . . . ?
N1 C1 C2 S1 -0.84(13) . . . . ?
N1 C1 C2 C5 179.96(8) . . . . ?
N1 C1 C8 C9 0.76(12) . . . . ?
N1 C1 C8 C7 179.81(8) . . . . ?
C1 N1 B1 C11 178.14(8) . . . . ?
C1 N1 B1 C10 -1.62(13) . . . . ?
C1 C2 C5 C6 0.39(13) . . . . ?
C1 C2 C5 C4 179.72(8) . . . . ?
C1 C8 C9 C10 -1.04(14) . . . . ?
C1 C8 C7 C6 0.08(13) . . . . ?
C2 S1 C3 C4 0.31(8) . . . . ?
C2 C1 C8 C9 -178.96(8) . . . . ?
C2 C1 C8 C7 0.09(12) . . . . ?
C8 C1 C2 S1 178.88(7) . . . . ?
C8 C1 C2 C5 -0.32(13) . . . . ?
C8 C9 C10 B1 -0.04(14) . . . . ?
C8 C7 C6 C5 -0.02(14) . . . . ?
C11 C12 C13 C14 -0.07(13) . . . . ?
C14 C13A C12A C11 0.12(13) . . . . ?
C14 C13A C12A C16A -177.83(8) . . . . ?
C13A C14 C13 C12 -1.08(13) . . . . ?
C9 C8 C7 C6 179.10(9) . . . . ?
C9 C10 B1 N1 1.29(13) . . . . ?
C9 C10 B1 C11 -178.45(9) . . . . ?
C12A C11 C12 C13 1.23(12) . . . . ?
C12A C11 C12 C16 179.17(8) . . . . ?
C12A C11 B1 N1 -61.41(11) . . . . ?
C12A C11 B1 C10 118.32(10) . . . . ?
C7 C8 C9 C10 179.94(8) . . . . ?
C7 C6 C5 C2 -0.21(13) . . . . ?
C7 C6 C5 C4 -179.41(9) . . . . ?
C12 C11 C12A C13A -1.26(12) . . . . ?
C12 C11 C12A C16A 176.63(8) . . . . ?
C12 C11 B1 N1 119.23(9) . . . . ?
C12 C11 B1 C10 -61.04(12) . . . . ?
C13 C14 C13A C12A 1.05(13) . . . . ?
C5 C4 C3 S1 -0.12(12) . . . . ?
C3 S1 C2 C1 -179.68(9) . . . . ?
C3 S1 C2 C5 -0.41(7) . . . . ?
C3 C4 C5 C2 -0.19(12) . . . . ?
C3 C4 C5 C6 179.06(9) . . . . ?
C16 C12 C13 C14 -178.05(8) . . . . ?
C15 C14 C13A C12A -178.76(9) . . . . ?
C15 C14 C13 C12 178.73(9) . . . . ?
B1 N1 C1 C2 -179.65(8) . . . . ?
B1 N1 C1 C8 0.64(13) . . . . ?
B1 C11 C12A C13A 179.36(8) . . . . ?
B1 C11 C12A C16A -2.75(12) . . . . ?
B1 C11 C12 C13 -179.39(8) . . . . ?
B1 C11 C12 C16 -1.45(13) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_appiariusy191014_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1998254'
loop_
_audit_author_name
_audit_author_address
'Enno Lork'
;University of Bremen
Germany
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-08-14 downloaded from the CCDC.
;
_audit_creation_date             2019-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yappiarius@uni-bremen.de
e.lork@uni-bremen.de
staubitz@uni-bremen.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H34 B2 N2, C Cl3 D'
_chemical_formula_sum            'C37 H34 B2 Cl3 D N2'
_chemical_formula_weight         636.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   20.9278(6)
_cell_length_b                   15.7312(5)
_cell_length_c                   9.9126(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.4570(10)
_cell_angle_gamma                90
_cell_volume                     3198.39(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      33.46
_cell_measurement_theta_min      2.495
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.7213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0856 before and 0.0469 after correction. The Ratio of minimum to maximum transmission is 0.9660. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            46636
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.500
_diffrn_reflns_theta_min         2.496
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3526
_reflns_number_total             4056
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+3.4005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) Cl3(0.5) C20(0.5) D20(0.5)
3.a Ternary CH refined with riding coordinates:
 C20(D20)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C13A(H13A)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N1 N 0.59645(5) 0.65388(6) 0.62510(10) 0.0142(2) Uani 1 1 d . . . . .
H1 H 0.5710(8) 0.6809(11) 0.6751(18) 0.025(4) Uiso 1 1 d . . . . .
C1 C 0.58927(5) 0.56660(7) 0.61599(11) 0.0130(2) Uani 1 1 d . . . . .
C2 C 0.54314(5) 0.52315(7) 0.68278(11) 0.0120(2) Uani 1 1 d . . . . .
C3 C 0.500000 0.56602(10) 0.750000 0.0125(3) Uani 1 2 d S T P . .
H3 H 0.499998 0.626405 0.749998 0.015 Uiso 1 2 calc RS T P . .
C4 C 0.500000 0.38952(10) 0.750000 0.0151(3) Uani 1 2 d S T P . .
H4 H 0.500001 0.329134 0.750003 0.018 Uiso 1 2 calc RS T P . .
C5 C 0.54180(5) 0.43215(7) 0.67970(11) 0.0136(2) Uani 1 1 d . . . . .
C6 C 0.58331(6) 0.38718(7) 0.60545(12) 0.0169(2) Uani 1 1 d . . . . .
H6 H 0.582679 0.326808 0.603620 0.020 Uiso 1 1 calc R . . . .
C7 C 0.62343(6) 0.43003(8) 0.53786(12) 0.0175(2) Uani 1 1 d . . . . .
H7 H 0.649284 0.399013 0.486256 0.021 Uiso 1 1 calc R . . . .
C8 C 0.62795(5) 0.52093(7) 0.54204(12) 0.0153(2) Uani 1 1 d . . . . .
C9 C 0.67242(6) 0.56495(8) 0.47347(13) 0.0191(2) Uani 1 1 d . . . . .
H9 H 0.697088 0.532846 0.420694 0.023 Uiso 1 1 calc R . . . .
C10 C 0.68075(6) 0.65066(8) 0.48082(13) 0.0202(3) Uani 1 1 d . . . . .
H10 H 0.710683 0.677754 0.434211 0.024 Uiso 1 1 calc R . . . .
C11 C 0.64885(5) 0.80152(7) 0.59159(12) 0.0141(2) Uani 1 1 d . . . . .
C12 C 0.62331(6) 0.86018(8) 0.48753(12) 0.0165(2) Uani 1 1 d . . . . .
C12A C 0.68607(6) 0.83309(8) 0.71507(12) 0.0160(2) Uani 1 1 d . . . . .
C13 C 0.63558(6) 0.94673(8) 0.50728(13) 0.0189(2) Uani 1 1 d . . . . .
H13 H 0.618119 0.985389 0.435806 0.023 Uiso 1 1 calc R . . . .
C13A C 0.69728(6) 0.92021(8) 0.73281(12) 0.0163(2) Uani 1 1 d . . . . .
H13A H 0.722146 0.940445 0.817449 0.020 Uiso 1 1 calc R . . . .
C14 C 0.67288(6) 0.97797(7) 0.62945(13) 0.0168(2) Uani 1 1 d . . . . .
C15 C 0.68879(7) 1.07129(8) 0.64689(15) 0.0246(3) Uani 1 1 d . . . . .
H15A H 0.699934 1.085100 0.745167 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.650884 1.104885 0.603034 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.725882 1.084555 0.603796 0.037 Uiso 1 1 calc GR . . . .
C16 C 0.58170(7) 0.82911(9) 0.35458(14) 0.0248(3) Uani 1 1 d . . . . .
H16A H 0.605760 0.786144 0.313224 0.037 Uiso 1 1 calc GR . . . .
H16B H 0.570834 0.876984 0.290905 0.037 Uiso 1 1 calc GR . . . .
H16C H 0.541490 0.804018 0.373304 0.037 Uiso 1 1 calc GR . . . .
C16A C 0.71694(8) 0.77374(9) 0.82876(14) 0.0279(3) Uani 1 1 d . . . . .
H16D H 0.682760 0.743739 0.864471 0.042 Uiso 1 1 calc GR . . . .
H16E H 0.743841 0.806505 0.903068 0.042 Uiso 1 1 calc GR . . . .
H16F H 0.744302 0.732382 0.792691 0.042 Uiso 1 1 calc GR . . . .
B1 B 0.64128(6) 0.70243(8) 0.56505(14) 0.0154(3) Uani 1 1 d . . . . .
Cl1 Cl 0.55071(6) 0.79539(8) 0.88218(15) 0.0260(2) Uani 0.5 1 d . . . A -1
Cl2 Cl 0.46834(6) 0.81379(10) 0.61436(17) 0.0319(3) Uani 0.5 1 d . . . A -1
Cl3 Cl 0.48470(3) 0.95412(4) 0.80688(8) 0.03098(17) Uani 0.5 1 d . . . A -1
C20 C 0.52286(12) 0.86716(16) 0.7463(3) 0.0198(5) Uani 0.5 1 d . . . A -1
D20 D 0.561009 0.887887 0.708733 0.024 Uiso 0.5 1 calc R . . A -1


_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
N1 H1 0.903(18) . ?
N1 C1 1.3822(14) . ?
N1 B1 1.4281(16) . ?
C1 C2 1.4463(15) . ?
C1 C8 1.3945(15) . ?
C2 C3 1.3974(13) . ?
C2 C5 1.4321(15) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.3938(14) 2_656 ?
C4 C5 1.3937(14) . ?
C5 C6 1.4320(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3533(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.4332(16) . ?
C8 C9 1.4349(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3596(18) . ?
C10 H10 0.9500 . ?
C10 B1 1.5221(18) . ?
C11 C12 1.4080(16) . ?
C11 C12A 1.4045(16) . ?
C11 B1 1.5836(17) . ?
C12 C13 1.3921(17) . ?
C12 C16 1.5093(17) . ?
C12A C13A 1.3958(16) . ?
C12A C16A 1.5065(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3935(17) . ?
C13A H13A 0.9500 . ?
C13A C14 1.3886(17) . ?
C14 C15 1.5077(17) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
Cl1 C20 1.766(3) . ?
Cl2 C20 1.767(3) . ?
Cl3 C20 1.749(3) . ?
C20 D20 1.0000 . ?

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 N1 H1 115.8(11) . . ?
C1 N1 B1 125.16(10) . . ?
B1 N1 H1 119.0(11) . . ?
N1 C1 C2 120.89(10) . . ?
N1 C1 C8 118.63(10) . . ?
C8 C1 C2 120.48(10) . . ?
C3 C2 C1 122.92(11) . . ?
C3 C2 C5 118.74(11) . . ?
C5 C2 C1 118.34(10) . . ?
C2 C3 C2 122.29(14) 2_656 . ?
C2 C3 H3 118.9 . . ?
C2 C3 H3 118.9 2_656 . ?
C5 C4 H4 118.8 2_656 . ?
C5 C4 H4 118.8 . . ?
C5 C4 C5 122.49(15) . 2_656 ?
C2 C5 C6 119.56(10) . . ?
C4 C5 C2 118.81(11) . . ?
C4 C5 C6 121.63(11) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.52(11) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.77(11) . . ?
C8 C7 H7 119.1 . . ?
C1 C8 C7 119.16(11) . . ?
C1 C8 C9 119.95(11) . . ?
C7 C8 C9 120.88(11) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 C8 122.79(11) . . ?
C10 C9 H9 118.6 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 B1 118.83(11) . . ?
B1 C10 H10 120.6 . . ?
C12 C11 B1 120.84(11) . . ?
C12A C11 C12 118.09(11) . . ?
C12A C11 B1 120.84(10) . . ?
C11 C12 C16 119.78(11) . . ?
C13 C12 C11 120.36(11) . . ?
C13 C12 C16 119.85(11) . . ?
C11 C12A C16A 120.93(11) . . ?
C13A C12A C11 120.48(11) . . ?
C13A C12A C16A 118.55(11) . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.53(11) . . ?
C14 C13 H13 119.2 . . ?
C12A C13A H13A 119.3 . . ?
C14 C13A C12A 121.44(11) . . ?
C14 C13A H13A 119.3 . . ?
C13 C14 C15 121.06(11) . . ?
C13A C14 C13 118.09(11) . . ?
C13A C14 C15 120.80(11) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12A C16A H16D 109.5 . . ?
C12A C16A H16E 109.5 . . ?
C12A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
N1 B1 C10 114.56(11) . . ?
N1 B1 C11 120.63(11) . . ?
C10 B1 C11 124.78(11) . . ?
Cl1 C20 Cl2 109.11(14) . . ?
Cl1 C20 D20 109.0 . . ?
Cl2 C20 D20 109.0 . . ?
Cl3 C20 Cl1 109.99(15) . . ?
Cl3 C20 Cl2 110.73(15) . . ?
Cl3 C20 D20 109.0 . . ?

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
N1 C1 C2 C3 5.24(16) . . . . ?
N1 C1 C2 C5 -174.73(10) . . . . ?
N1 C1 C8 C7 176.76(10) . . . . ?
N1 C1 C8 C9 -2.12(16) . . . . ?
C1 N1 B1 C10 2.66(17) . . . . ?
C1 N1 B1 C11 -175.46(11) . . . . ?
C1 C2 C3 C2 -178.28(12) . . . 2_656 ?
C1 C2 C5 C4 176.60(8) . . . . ?
C1 C2 C5 C6 -3.16(16) . . . . ?
C1 C8 C9 C10 2.42(19) . . . . ?
C2 C1 C8 C7 -2.62(17) . . . . ?
C2 C1 C8 C9 178.50(11) . . . . ?
C2 C5 C6 C7 -0.32(17) . . . . ?
C3 C2 C5 C4 -3.37(14) . . . . ?
C3 C2 C5 C6 176.87(9) . . . . ?
C4 C5 C6 C7 179.93(10) . . . . ?
C5 C2 C3 C2 1.69(7) . . . 2_656 ?
C5 C4 C5 C2 1.70(7) 2_656 . . . ?
C5 C4 C5 C6 -178.55(12) 2_656 . . . ?
C5 C6 C7 C8 2.47(18) . . . . ?
C6 C7 C8 C1 -0.99(18) . . . . ?
C6 C7 C8 C9 177.87(11) . . . . ?
C7 C8 C9 C10 -176.44(12) . . . . ?
C8 C1 C2 C3 -175.40(9) . . . . ?
C8 C1 C2 C5 4.63(16) . . . . ?
C8 C9 C10 B1 -0.09(19) . . . . ?
C9 C10 B1 N1 -2.29(18) . . . . ?
C9 C10 B1 C11 175.74(12) . . . . ?
C11 C12 C13 C14 -0.27(19) . . . . ?
C11 C12A C13A C14 -0.73(18) . . . . ?
C12 C11 C12A C13A -0.20(17) . . . . ?
C12 C11 C12A C16A -177.74(11) . . . . ?
C12 C11 B1 N1 -106.47(13) . . . . ?
C12 C11 B1 C10 75.61(16) . . . . ?
C12 C13 C14 C13A -0.64(18) . . . . ?
C12 C13 C14 C15 176.76(12) . . . . ?
C12A C11 C12 C13 0.69(17) . . . . ?
C12A C11 C12 C16 -178.53(11) . . . . ?
C12A C11 B1 N1 79.17(15) . . . . ?
C12A C11 B1 C10 -98.75(15) . . . . ?
C12A C13A C14 C13 1.13(18) . . . . ?
C12A C13A C14 C15 -176.27(11) . . . . ?
C16 C12 C13 C14 178.95(12) . . . . ?
C16A C12A C13A C14 176.87(12) . . . . ?
B1 N1 C1 C2 178.87(11) . . . . ?
B1 N1 C1 C8 -0.50(17) . . . . ?
B1 C11 C12 C13 -173.83(11) . . . . ?
B1 C11 C12 C16 6.96(17) . . . . ?
B1 C11 C12A C13A 174.31(11) . . . . ?
B1 C11 C12A C16A -3.22(18) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
