# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo200904a
_database_code_depnum_ccdc_archive 'CCDC 2142887'
loop_
_audit_author_name
_audit_author_address
'Lizhi Gai'
;Hanghzou Normal University
China
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_audit_creation_date             2022-01-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 B F2 N2 O'
_chemical_formula_sum            'C14 H9 B F2 N2 O'
_chemical_formula_weight         270.04
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7662(11)
_cell_length_b                   20.908(3)
_cell_length_c                   7.2899(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.463(3)
_cell_angle_gamma                90
_cell_volume                     1183.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2236
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.25
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0636 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.8912.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12907
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.388
_diffrn_reflns_theta_min         1.948
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1785
_reflns_number_total             2955
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0733
_refine_ls_restrained_S_all      1.025
_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)+(0.0937P)²+0.9953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.2239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 N1, B1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F1 F 0.4313(3) 0.43436(10) 0.4712(4) 0.0955(9) Uani 1 1 d . . . . .
F2 F 0.4706(3) 0.43991(11) 0.1644(4) 0.0978(10) Uani 1 1 d . . . . .
O1 O 0.0807(3) 0.21408(12) 0.1742(4) 0.0726(8) Uani 1 1 d . . . . .
N1 N 0.3275(3) 0.34797(11) 0.2877(3) 0.0429(6) Uani 1 1 d . U . . .
N2 N 0.1856(3) 0.45552(12) 0.2770(3) 0.0488(6) Uani 1 1 d . . . . .
C1 C 0.1858(5) 0.51886(17) 0.3096(5) 0.0626(9) Uani 1 1 d . . . . .
H1 H 0.288000 0.538142 0.347223 0.075 Uiso 1 1 calc R U . . .
C2 C 0.0438(6) 0.55567(18) 0.2899(5) 0.0756(12) Uani 1 1 d . . . . .
H2 H 0.047830 0.599305 0.314353 0.091 Uiso 1 1 calc R U . . .
C3 C -0.1087(6) 0.5266(2) 0.2322(5) 0.0756(12) Uani 1 1 d . . . . .
H3 H -0.208160 0.550808 0.216340 0.091 Uiso 1 1 calc R U . . .
C4 C -0.1109(4) 0.46282(19) 0.1992(5) 0.0642(10) Uani 1 1 d . . . . .
H4 H -0.212651 0.443200 0.161505 0.077 Uiso 1 1 calc R U . . .
C5 C 0.0378(4) 0.42650(16) 0.2214(4) 0.0485(7) Uani 1 1 d . . . . .
C6 C 0.0369(4) 0.35869(16) 0.1928(5) 0.0550(8) Uani 1 1 d . . . . .
H6 H -0.062491 0.339074 0.148321 0.066 Uiso 1 1 calc R U . . .
C7 C 0.1755(4) 0.32320(15) 0.2286(4) 0.0470(7) Uani 1 1 d . . . . .
C8 C 0.1933(4) 0.25082(15) 0.2243(4) 0.0509(7) Uani 1 1 d . . . . .
C9 C 0.3660(4) 0.23828(14) 0.2902(4) 0.0467(7) Uani 1 1 d . . . . .
C10 C 0.4558(5) 0.18202(15) 0.3197(4) 0.0564(8) Uani 1 1 d . . . . .
H10 H 0.404403 0.142525 0.298257 0.068 Uiso 1 1 calc R U . . .
C11 C 0.6233(5) 0.18607(17) 0.3814(5) 0.0614(9) Uani 1 1 d . . . . .
H11 H 0.686190 0.148825 0.401432 0.074 Uiso 1 1 calc R U . . .
C12 C 0.6995(4) 0.24491(17) 0.4142(5) 0.0580(8) Uani 1 1 d . . . . .
H12 H 0.812674 0.246375 0.456527 0.070 Uiso 1 1 calc R U . . .
C13 C 0.6111(4) 0.30163(15) 0.3854(4) 0.0495(7) Uani 1 1 d . . . . .
H13 H 0.663178 0.341030 0.406576 0.059 Uiso 1 1 calc R U . . .
C14 C 0.4439(4) 0.29746(13) 0.3244(4) 0.0429(7) Uani 1 1 d . . . . .
B1 B 0.3659(5) 0.41827(18) 0.3021(6) 0.0531(9) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.372(4) . ?
F2 B1 1.373(5) . ?
O1 C8 1.218(4) . ?
N1 C7 1.356(4) . ?
N1 C14 1.414(4) . ?
N1 B1 1.503(4) . ?
N2 C1 1.346(4) . ?
N2 C5 1.357(4) . ?
N2 B1 1.612(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.351(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(4) . ?
C5 C6 1.433(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.332(4) . ?
C7 C8 1.520(4) . ?
C8 C9 1.445(4) . ?
C9 C10 1.384(4) . ?
C9 C14 1.399(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C14 109.1(2) . . ?
C7 N1 B1 124.6(3) . . ?
C14 N1 B1 126.2(2) . . ?
C1 N2 C5 119.5(3) . . ?
C1 N2 B1 117.1(3) . . ?
C5 N2 B1 123.4(3) . . ?
N2 C1 H1 118.6 . . ?
N2 C1 C2 122.8(4) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.3(4) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(4) . . ?
C5 C4 H4 119.8 . . ?
N2 C5 C4 119.3(3) . . ?
N2 C5 C6 119.3(3) . . ?
C4 C5 C6 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.3 . . ?
N1 C7 C8 108.0(3) . . ?
C6 C7 N1 123.3(3) . . ?
C6 C7 C8 128.6(3) . . ?
O1 C8 C7 124.7(3) . . ?
O1 C8 C9 130.3(3) . . ?
C9 C8 C7 104.9(2) . . ?
C10 C9 C8 132.2(3) . . ?
C10 C9 C14 120.5(3) . . ?
C14 C9 C8 107.3(3) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.6(3) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 121.3 . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 H13 121.3 . . ?
C9 C14 N1 110.6(2) . . ?
C13 C14 N1 128.0(3) . . ?
C13 C14 C9 121.4(3) . . ?
F1 B1 F2 111.1(3) . . ?
F1 B1 N1 112.0(3) . . ?
F1 B1 N2 107.4(3) . . ?
F2 B1 N1 112.9(3) . . ?
F2 B1 N2 106.1(3) . . ?
N1 B1 N2 107.0(2) . . ?

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 C8 C9 C10 -1.2(6) . . . . ?
O1 C8 C9 C14 178.2(3) . . . . ?
N1 C7 C8 O1 -178.5(3) . . . . ?
N1 C7 C8 C9 1.4(3) . . . . ?
N2 C1 C2 C3 -0.5(6) . . . . ?
N2 C5 C6 C7 3.5(5) . . . . ?
C1 N2 C5 C4 0.0(4) . . . . ?
C1 N2 C5 C6 -177.9(3) . . . . ?
C1 N2 B1 F1 50.9(4) . . . . ?
C1 N2 B1 F2 -67.9(4) . . . . ?
C1 N2 B1 N1 171.3(3) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 N2 0.2(5) . . . . ?
C3 C4 C5 C6 178.0(3) . . . . ?
C4 C5 C6 C7 -174.4(3) . . . . ?
C5 N2 C1 C2 0.2(5) . . . . ?
C5 N2 B1 F1 -130.7(3) . . . . ?
C5 N2 B1 F2 110.5(3) . . . . ?
C5 N2 B1 N1 -10.3(4) . . . . ?
C5 C6 C7 N1 -2.4(5) . . . . ?
C5 C6 C7 C8 173.6(3) . . . . ?
C6 C7 C8 O1 5.0(6) . . . . ?
C6 C7 C8 C9 -175.1(3) . . . . ?
C7 N1 C14 C9 -0.6(3) . . . . ?
C7 N1 C14 C13 179.6(3) . . . . ?
C7 N1 B1 F1 129.1(3) . . . . ?
C7 N1 B1 F2 -104.6(3) . . . . ?
C7 N1 B1 N2 11.7(4) . . . . ?
C7 C8 C9 C10 178.9(3) . . . . ?
C7 C8 C9 C14 -1.7(3) . . . . ?
C8 C9 C10 C11 178.8(3) . . . . ?
C8 C9 C14 N1 1.5(3) . . . . ?
C8 C9 C14 C13 -178.7(3) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C9 C14 N1 -179.0(3) . . . . ?
C10 C9 C14 C13 0.8(4) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 N1 179.0(3) . . . . ?
C12 C13 C14 C9 -0.8(4) . . . . ?
C14 N1 C7 C6 176.1(3) . . . . ?
C14 N1 C7 C8 -0.5(3) . . . . ?
C14 N1 B1 F1 -54.0(4) . . . . ?
C14 N1 B1 F2 72.2(4) . . . . ?
C14 N1 B1 N2 -171.5(2) . . . . ?
C14 C9 C10 C11 -0.6(5) . . . . ?
B1 N1 C7 C6 -6.5(5) . . . . ?
B1 N1 C7 C8 176.8(3) . . . . ?
B1 N1 C14 C9 -177.8(3) . . . . ?
B1 N1 C14 C13 2.3(5) . . . . ?
B1 N2 C1 C2 178.7(3) . . . . ?
B1 N2 C5 C4 -178.4(3) . . . . ?
B1 N2 C5 C6 3.7(4) . . . . ?

_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_mo200905b
_database_code_depnum_ccdc_archive 'CCDC 2142888'
loop_
_audit_author_name
_audit_author_address
'Lizhi Gai'
;Hanghzou Normal University
China
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 B F2 N2 O S'
_chemical_formula_sum            'C16 H9 B F2 N2 O S'
_chemical_formula_weight         326.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.763(3)
_cell_length_b                   24.877(10)
_cell_length_c                   7.273(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.525(12)
_cell_angle_gamma                90
_cell_volume                     1404.4(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    751
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0605 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10141
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.637
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2130
_reflns_number_total             2709
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0807
_refine_ls_restrained_S_all      1.125
_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)+(0.0474P)²+5.6879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2140
_refine_ls_wR_factor_ref         0.2198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_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 0.67270(18) 0.55475(6) 0.8268(2) 0.0515(4) Uani 1 1 d . . . . .
F1 F 0.0700(5) 0.58894(14) 0.8705(7) 0.0785(13) Uani 1 1 d . . . . .
F2 F 0.1018(5) 0.59046(14) 0.5621(6) 0.0743(12) Uani 1 1 d . . . . .
O1 O 0.4714(6) 0.77525(16) 0.8506(7) 0.0660(13) Uani 1 1 d . . . . .
N1 N 0.3527(5) 0.57366(16) 0.7540(6) 0.0384(10) Uani 1 1 d . . . . .
N2 N 0.2171(5) 0.66389(16) 0.7366(6) 0.0399(10) Uani 1 1 d . . . . .
C1 C 0.3725(7) 0.5177(2) 0.7294(7) 0.0450(12) Uani 1 1 d . . . . .
C2 C 0.2453(8) 0.4815(2) 0.6785(8) 0.0520(14) Uani 1 1 d . . . . .
H2 H 0.1322 0.4923 0.6572 0.062 Uiso 1 1 calc R U . . .
C3 C 0.2956(11) 0.4281(2) 0.6608(9) 0.0681(19) Uani 1 1 d . . . . .
H3 H 0.2132 0.4028 0.6268 0.082 Uiso 1 1 calc R U . . .
C4 C 0.4605(10) 0.4114(2) 0.6913(9) 0.0660(18) Uani 1 1 d . . . . .
H4 H 0.4881 0.3754 0.6750 0.079 Uiso 1 1 calc R U . . .
C5 C 0.5879(9) 0.4472(2) 0.7461(9) 0.0617(17) Uani 1 1 d . . . . .
H5 H 0.7001 0.4358 0.7700 0.074 Uiso 1 1 calc R U . . .
C6 C 0.5403(7) 0.5008(2) 0.7638(8) 0.0473(13) Uani 1 1 d . . . . .
C7 C 0.4998(6) 0.5979(2) 0.8050(7) 0.0413(12) Uani 1 1 d . . . . .
C8 C 0.5108(6) 0.6539(2) 0.8329(7) 0.0413(12) Uani 1 1 d . . . . .
H8 H 0.6122 0.6695 0.8765 0.050 Uiso 1 1 calc R U . . .
C9 C 0.3707(6) 0.6846(2) 0.7949(7) 0.0408(12) Uani 1 1 d . . . . .
C10 C 0.3591(7) 0.7458(2) 0.8004(7) 0.0424(12) Uani 1 1 d . . . . .
C11 C 0.0951(7) 0.8047(2) 0.7016(8) 0.0501(13) Uani 1 1 d . . . . .
H11 H 0.1483 0.8376 0.7222 0.060 Uiso 1 1 calc R U . . .
C12 C -0.1511(7) 0.7528(2) 0.6086(8) 0.0512(14) Uani 1 1 d . . . . .
H12 H -0.2645 0.7522 0.5662 0.061 Uiso 1 1 calc R U . . .
C13 C -0.0731(8) 0.8016(2) 0.6393(8) 0.0538(15) Uani 1 1 d . . . . .
H13 H -0.1347 0.8331 0.6179 0.065 Uiso 1 1 calc R U . . .
C14 C -0.0658(7) 0.7040(2) 0.6390(7) 0.0456(12) Uani 1 1 d . . . . .
H14 H -0.1197 0.6711 0.6189 0.055 Uiso 1 1 calc R U . . .
C15 C 0.1034(6) 0.7074(2) 0.7005(7) 0.0394(11) Uani 1 1 d . . . . .
C16 C 0.1826(7) 0.7563(2) 0.7324(7) 0.0420(12) Uani 1 1 d . . . . .
B1 B 0.1749(8) 0.6037(3) 0.7286(10) 0.0473(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.749(6) . ?
S1 C7 1.724(5) . ?
F1 B1 1.370(8) . ?
F2 B1 1.372(8) . ?
O1 C10 1.193(6) . ?
N1 C1 1.412(7) . ?
N1 C7 1.340(6) . ?
N1 B1 1.579(7) . ?
N2 C9 1.363(6) . ?
N2 C15 1.420(6) . ?
N2 B1 1.534(7) . ?
C1 C2 1.385(8) . ?
C1 C6 1.389(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(8) . ?
C7 C8 1.412(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.354(7) . ?
C9 C10 1.528(7) . ?
C10 C16 1.475(7) . ?
C11 H11 0.9300 . ?
C11 C13 1.380(8) . ?
C11 C16 1.398(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(8) . ?
C12 C14 1.400(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.387(7) . ?
C15 C16 1.383(7) . ?

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
C7 S1 C6 89.9(3) . . ?
C1 N1 B1 123.2(4) . . ?
C7 N1 C1 112.7(4) . . ?
C7 N1 B1 124.2(4) . . ?
C9 N2 C15 108.1(4) . . ?
C9 N2 B1 124.5(4) . . ?
C15 N2 B1 127.2(4) . . ?
C2 C1 N1 126.7(5) . . ?
C2 C1 C6 121.1(5) . . ?
C6 C1 N1 112.2(5) . . ?
C1 C2 H2 121.7 . . ?
C1 C2 C3 116.5(6) . . ?
C3 C2 H2 121.7 . . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.7(6) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(6) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 121.5 . . ?
C4 C5 C6 116.9(6) . . ?
C6 C5 H5 121.5 . . ?
C1 C6 S1 111.2(4) . . ?
C1 C6 C5 121.6(6) . . ?
C5 C6 S1 127.2(5) . . ?
N1 C7 S1 114.0(4) . . ?
N1 C7 C8 122.3(4) . . ?
C8 C7 S1 123.7(4) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.6(4) . . ?
C9 C8 H8 120.7 . . ?
N2 C9 C10 109.4(4) . . ?
C8 C9 N2 123.4(5) . . ?
C8 C9 C10 127.1(4) . . ?
O1 C10 C9 125.2(5) . . ?
O1 C10 C16 131.9(5) . . ?
C16 C10 C9 102.9(4) . . ?
C13 C11 H11 121.2 . . ?
C13 C11 C16 117.5(5) . . ?
C16 C11 H11 121.2 . . ?
C13 C12 H12 118.9 . . ?
C13 C12 C14 122.3(5) . . ?
C14 C12 H12 118.9 . . ?
C11 C13 H13 119.5 . . ?
C12 C13 C11 121.0(5) . . ?
C12 C13 H13 119.5 . . ?
C12 C14 H14 121.9 . . ?
C15 C14 C12 116.3(5) . . ?
C15 C14 H14 121.9 . . ?
C14 C15 N2 126.7(5) . . ?
C16 C15 N2 111.4(4) . . ?
C16 C15 C14 121.8(5) . . ?
C11 C16 C10 130.9(5) . . ?
C15 C16 C10 108.1(4) . . ?
C15 C16 C11 121.0(5) . . ?
F1 B1 F2 110.9(5) . . ?
F1 B1 N1 108.1(5) . . ?
F1 B1 N2 111.2(5) . . ?
F2 B1 N1 110.1(5) . . ?
F2 B1 N2 110.7(5) . . ?
N2 B1 N1 105.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C7 C8 C9 173.8(4) . . . . ?
O1 C10 C16 C11 2.1(11) . . . . ?
O1 C10 C16 C15 -177.3(6) . . . . ?
N1 C1 C2 C3 179.3(5) . . . . ?
N1 C1 C6 S1 0.0(6) . . . . ?
N1 C1 C6 C5 -179.5(5) . . . . ?
N1 C7 C8 C9 -4.5(8) . . . . ?
N2 C9 C10 O1 177.8(6) . . . . ?
N2 C9 C10 C16 -1.7(6) . . . . ?
N2 C15 C16 C10 -2.0(6) . . . . ?
N2 C15 C16 C11 178.5(5) . . . . ?
C1 N1 C7 S1 0.0(6) . . . . ?
C1 N1 C7 C8 178.4(5) . . . . ?
C1 N1 B1 F1 70.0(6) . . . . ?
C1 N1 B1 F2 -51.3(7) . . . . ?
C1 N1 B1 N2 -170.9(4) . . . . ?
C1 C2 C3 C4 0.0(10) . . . . ?
C2 C1 C6 S1 -179.6(4) . . . . ?
C2 C1 C6 C5 0.9(9) . . . . ?
C2 C3 C4 C5 1.4(11) . . . . ?
C3 C4 C5 C6 -1.6(10) . . . . ?
C4 C5 C6 S1 -179.0(5) . . . . ?
C4 C5 C6 C1 0.4(9) . . . . ?
C6 S1 C7 N1 0.0(4) . . . . ?
C6 S1 C7 C8 -178.4(5) . . . . ?
C6 C1 C2 C3 -1.1(8) . . . . ?
C7 S1 C6 C1 0.0(4) . . . . ?
C7 S1 C6 C5 179.4(6) . . . . ?
C7 N1 C1 C2 179.5(5) . . . . ?
C7 N1 C1 C6 0.0(6) . . . . ?
C7 N1 B1 F1 -108.4(6) . . . . ?
C7 N1 B1 F2 130.3(5) . . . . ?
C7 N1 B1 N2 10.7(7) . . . . ?
C7 C8 C9 N2 2.2(8) . . . . ?
C7 C8 C9 C10 -174.7(5) . . . . ?
C8 C9 C10 O1 -4.9(10) . . . . ?
C8 C9 C10 C16 175.5(5) . . . . ?
C9 N2 C15 C14 -179.9(5) . . . . ?
C9 N2 C15 C16 0.9(6) . . . . ?
C9 N2 B1 F1 104.0(6) . . . . ?
C9 N2 B1 F2 -132.3(5) . . . . ?
C9 N2 B1 N1 -13.0(7) . . . . ?
C9 C10 C16 C11 -178.4(6) . . . . ?
C9 C10 C16 C15 2.2(6) . . . . ?
C12 C14 C15 N2 -178.4(5) . . . . ?
C12 C14 C15 C16 0.8(8) . . . . ?
C13 C11 C16 C10 -178.9(6) . . . . ?
C13 C11 C16 C15 0.4(8) . . . . ?
C13 C12 C14 C15 -0.6(8) . . . . ?
C14 C12 C13 C11 0.3(9) . . . . ?
C14 C15 C16 C10 178.7(5) . . . . ?
C14 C15 C16 C11 -0.8(8) . . . . ?
C15 N2 C9 C8 -176.8(5) . . . . ?
C15 N2 C9 C10 0.6(6) . . . . ?
C15 N2 B1 F1 -70.4(7) . . . . ?
C15 N2 B1 F2 53.3(7) . . . . ?
C15 N2 B1 N1 172.5(4) . . . . ?
C16 C11 C13 C12 -0.2(9) . . . . ?
B1 N1 C1 C2 1.0(8) . . . . ?
B1 N1 C1 C6 -178.6(5) . . . . ?
B1 N1 C7 S1 178.5(4) . . . . ?
B1 N1 C7 C8 -3.0(8) . . . . ?
B1 N2 C9 C8 7.8(9) . . . . ?
B1 N2 C9 C10 -174.8(5) . . . . ?
B1 N2 C15 C14 -4.7(9) . . . . ?
B1 N2 C15 C16 176.1(5) . . . . ?

_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_mo200915a
_database_code_depnum_ccdc_archive 'CCDC 2142890'
loop_
_audit_author_name
_audit_author_address
'Lizhi Gai'
;Hanghzou Normal University
China
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_audit_creation_date             2022-01-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H21 B N2 O'
_chemical_formula_sum            'C30 H21 B N2 O'
_chemical_formula_weight         436.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   17.675(3)
_cell_length_b                   17.675(3)
_cell_length_c                   29.023(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9067(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2218
_cell_measurement_temperature    302.45
_cell_measurement_theta_max      23.068
_cell_measurement_theta_min      2.304
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0781 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.8752.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            33614
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.349
_diffrn_ambient_temperature      302.45
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1963
_reflns_number_total             4013
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     312
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      0.999
_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)+(0.0873P)²+7.1535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.2155
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.0914(2) 0.1318(2) 0.56263(12) 0.1278(13) Uani 1 1 d . . . . .
N1 N 0.22899(15) 0.38873(15) 0.56133(8) 0.0610(7) Uani 1 1 d . . . . .
N2 N 0.25053(15) 0.24630(15) 0.56290(9) 0.0604(7) Uani 1 1 d . . . . .
C1 C 0.2839(2) 0.17387(19) 0.56376(11) 0.0648(9) Uani 1 1 d . . . . .
C2 C 0.3597(2) 0.15640(19) 0.56496(13) 0.0807(11) Uani 1 1 d . . . . .
H2 H 0.396589 0.193907 0.564688 0.097 Uiso 1 1 calc R U . . .
C3 C 0.3787(3) 0.0797(2) 0.56659(16) 0.1093(15) Uani 1 1 d . . . . .
H3 H 0.429469 0.065935 0.567845 0.131 Uiso 1 1 calc R U . . .
C4 C 0.3234(4) 0.0232(2) 0.56640(16) 0.1149(17) Uani 1 1 d . . . . .
H4 H 0.337266 -0.027520 0.567238 0.138 Uiso 1 1 calc R U . . .
C5 C 0.2480(4) 0.0432(3) 0.56494(14) 0.1084(15) Uani 1 1 d . U . . .
H5 H 0.210689 0.006086 0.564545 0.130 Uiso 1 1 calc R U . . .
C6 C 0.2284(3) 0.1180(2) 0.56410(12) 0.0827(11) Uani 1 1 d . . . . .
C7 C 0.1548(3) 0.1563(2) 0.56352(12) 0.0838(11) Uani 1 1 d . . . . .
C8 C 0.1746(2) 0.2387(2) 0.56360(11) 0.0693(9) Uani 1 1 d . . . . .
C9 C 0.1271(2) 0.2980(3) 0.56493(12) 0.0777(10) Uani 1 1 d . . . . .
H9 H 0.075238 0.289251 0.566362 0.093 Uiso 1 1 calc R U . . .
C10 C 0.1537(2) 0.3735(2) 0.56422(11) 0.0688(9) Uani 1 1 d . . . . .
C11 C 0.0990(3) 0.4334(3) 0.56620(13) 0.0908(12) Uani 1 1 d . . . . .
H11 H 0.047715 0.422268 0.568616 0.109 Uiso 1 1 calc R U . . .
C12 C 0.1231(3) 0.5075(3) 0.56450(15) 0.1057(14) Uani 1 1 d . . . . .
H12 H 0.087606 0.546256 0.565772 0.127 Uiso 1 1 calc R U . . .
C13 C 0.1987(3) 0.5251(2) 0.56095(13) 0.0904(12) Uani 1 1 d . . . . .
C14 C 0.2262(4) 0.6012(2) 0.55836(15) 0.1042(15) Uani 1 1 d . U . . .
H14 H 0.191978 0.641122 0.559751 0.125 Uiso 1 1 calc R U . . .
C15 C 0.3005(4) 0.6160(3) 0.55395(17) 0.1207(18) Uani 1 1 d . . . . .
H15 H 0.317463 0.665693 0.551918 0.145 Uiso 1 1 calc R U . . .
C16 C 0.3504(3) 0.5579(2) 0.55249(15) 0.1075(15) Uani 1 1 d . . . . .
H16 H 0.401713 0.568516 0.549594 0.129 Uiso 1 1 calc R U . . .
C17 C 0.3275(3) 0.4837(2) 0.55517(13) 0.0792(11) Uani 1 1 d . . . . .
H17 H 0.363723 0.445556 0.554195 0.095 Uiso 1 1 calc R U . . .
C18 C 0.2521(2) 0.46422(19) 0.55927(11) 0.0679(9) Uani 1 1 d . . . . .
C19 C 0.33021(18) 0.32454(16) 0.50723(11) 0.0552(8) Uani 1 1 d . . . . .
C20 C 0.2808(2) 0.32458(19) 0.47023(12) 0.0707(10) Uani 1 1 d . . . . .
H20 H 0.229216 0.325991 0.476337 0.085 Uiso 1 1 calc R U . . .
C21 C 0.3036(3) 0.3227(2) 0.42503(13) 0.0823(11) Uani 1 1 d . . . . .
H21 H 0.267676 0.322088 0.401637 0.099 Uiso 1 1 calc R U . . .
C22 C 0.3781(3) 0.3216(2) 0.41431(15) 0.0891(12) Uani 1 1 d . . . . .
H22 H 0.394041 0.321768 0.383778 0.107 Uiso 1 1 calc R U . . .
C23 C 0.4282(3) 0.3202(3) 0.44888(17) 0.1120(16) Uani 1 1 d . . . . .
H23 H 0.479565 0.318080 0.442084 0.134 Uiso 1 1 calc R U . . .
C24 C 0.4054(2) 0.3219(3) 0.49453(14) 0.0995(14) Uani 1 1 d . . . . .
H24 H 0.442100 0.321281 0.517476 0.119 Uiso 1 1 calc R U . . .
C25 C 0.34603(18) 0.32898(17) 0.60514(11) 0.0582(8) Uani 1 1 d . . . . .
C26 C 0.4225(2) 0.3389(3) 0.60857(15) 0.1075(15) Uani 1 1 d . . . . .
H26 H 0.450072 0.347054 0.581738 0.129 Uiso 1 1 calc R U . . .
C27 C 0.4611(3) 0.3374(3) 0.6506(2) 0.136(2) Uani 1 1 d . . . . .
H27 H 0.513437 0.343120 0.651121 0.163 Uiso 1 1 calc R U . . .
C28 C 0.4229(3) 0.3278(3) 0.69025(17) 0.1076(16) Uani 1 1 d . . . . .
H28 H 0.448505 0.326704 0.718245 0.129 Uiso 1 1 calc R U . . .
C29 C 0.3479(3) 0.3199(2) 0.68896(14) 0.0961(13) Uani 1 1 d . . . . .
H29 H 0.320815 0.314196 0.716200 0.115 Uiso 1 1 calc R U . . .
C30 C 0.3103(2) 0.3203(2) 0.64711(13) 0.0800(11) Uani 1 1 d . . . . .
H30 H 0.258055 0.314289 0.647277 0.096 Uiso 1 1 calc R U . . .
B1 B 0.2945(2) 0.3226(2) 0.55900(13) 0.0558(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.201(5) . ?
N1 C10 1.360(4) . ?
N1 C18 1.397(4) . ?
N1 B1 1.647(5) . ?
N2 C1 1.410(4) . ?
N2 C8 1.349(4) . ?
N2 B1 1.560(4) . ?
C1 C2 1.376(5) . ?
C1 C6 1.392(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(6) . ?
C6 C7 1.468(6) . ?
C7 C8 1.499(5) . ?
C8 C9 1.344(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.414(5) . ?
C10 C11 1.435(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(7) . ?
C13 C14 1.432(6) . ?
C13 C18 1.432(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.346(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.354(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C19 C20 1.384(4) . ?
C19 C24 1.379(5) . ?
C19 B1 1.630(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.352(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.338(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.385(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.366(5) . ?
C25 C30 1.380(5) . ?
C25 B1 1.624(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.398(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.346(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.334(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.384(5) . ?
C30 H30 0.9300 . ?

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
C10 N1 C18 118.6(3) . . ?
C10 N1 B1 123.3(3) . . ?
C18 N1 B1 118.1(3) . . ?
C1 N2 B1 125.3(3) . . ?
C8 N2 C1 109.0(3) . . ?
C8 N2 B1 125.6(3) . . ?
C2 C1 N2 127.7(3) . . ?
C2 C1 C6 121.8(4) . . ?
C6 C1 N2 110.5(4) . . ?
C1 C2 H2 121.5 . . ?
C1 C2 C3 117.0(4) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(5) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(5) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C7 107.3(4) . . ?
C5 C6 C1 120.6(5) . . ?
C5 C6 C7 132.1(4) . . ?
O1 C7 C6 131.4(4) . . ?
O1 C7 C8 124.7(5) . . ?
C6 C7 C8 104.0(3) . . ?
N2 C8 C7 109.2(4) . . ?
C9 C8 N2 123.0(3) . . ?
C9 C8 C7 127.7(4) . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
N1 C10 C9 120.9(3) . . ?
N1 C10 C11 121.0(4) . . ?
C9 C10 C11 118.0(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 123.0(5) . . ?
C12 C13 C18 118.2(4) . . ?
C18 C13 C14 118.7(5) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(5) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(5) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.0 . . ?
C15 C16 C17 122.0(5) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.8(4) . . ?
C18 C17 H17 119.1 . . ?
N1 C18 C13 121.5(4) . . ?
C17 C18 N1 121.6(3) . . ?
C17 C18 C13 116.9(4) . . ?
C20 C19 B1 118.1(3) . . ?
C24 C19 C20 113.6(3) . . ?
C24 C19 B1 128.2(3) . . ?
C19 C20 H20 118.1 . . ?
C21 C20 C19 123.8(4) . . ?
C21 C20 H20 118.1 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.9 . . ?
C23 C22 C21 118.2(4) . . ?
C23 C22 H22 120.9 . . ?
C22 C23 H23 119.2 . . ?
C22 C23 C24 121.6(4) . . ?
C24 C23 H23 119.2 . . ?
C19 C24 C23 122.5(4) . . ?
C19 C24 H24 118.8 . . ?
C23 C24 H24 118.8 . . ?
C26 C25 C30 113.7(3) . . ?
C26 C25 B1 128.6(3) . . ?
C30 C25 B1 117.6(3) . . ?
C25 C26 H26 118.5 . . ?
C25 C26 C27 123.0(5) . . ?
C27 C26 H26 118.5 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(5) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.4 . . ?
C29 C28 C27 119.2(4) . . ?
C29 C28 H28 120.4 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.1(5) . . ?
C30 C29 H29 120.0 . . ?
C25 C30 C29 123.7(4) . . ?
C25 C30 H30 118.1 . . ?
C29 C30 H30 118.1 . . ?
N2 B1 N1 105.1(3) . . ?
N2 B1 C19 106.1(2) . . ?
N2 B1 C25 106.3(3) . . ?
C19 B1 N1 107.2(2) . . ?
C25 B1 N1 108.1(2) . . ?
C25 B1 C19 122.8(3) . . ?

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 C7 C8 N2 -177.6(4) . . . . ?
O1 C7 C8 C9 3.5(6) . . . . ?
N1 C10 C11 C12 0.9(5) . . . . ?
N2 C1 C2 C3 178.7(3) . . . . ?
N2 C1 C6 C5 -180.0(3) . . . . ?
N2 C1 C6 C7 -0.1(4) . . . . ?
N2 C8 C9 C10 2.0(5) . . . . ?
C1 N2 C8 C7 -1.8(3) . . . . ?
C1 N2 C8 C9 177.2(3) . . . . ?
C1 N2 B1 N1 -178.1(3) . . . . ?
C1 N2 B1 C19 68.5(4) . . . . ?
C1 N2 B1 C25 -63.7(4) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C1 C6 C7 O1 178.3(4) . . . . ?
C1 C6 C7 C8 -0.9(4) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
C2 C1 C6 C7 178.9(3) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C4 C5 C6 C1 1.3(6) . . . . ?
C4 C5 C6 C7 -178.5(4) . . . . ?
C5 C6 C7 O1 -1.9(7) . . . . ?
C5 C6 C7 C8 178.9(4) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C6 C7 C8 N2 1.6(4) . . . . ?
C6 C7 C8 C9 -177.3(3) . . . . ?
C7 C8 C9 C10 -179.2(3) . . . . ?
C8 N2 C1 C2 -177.7(3) . . . . ?
C8 N2 C1 C6 1.2(4) . . . . ?
C8 N2 B1 N1 5.5(4) . . . . ?
C8 N2 B1 C19 -107.9(3) . . . . ?
C8 N2 B1 C25 119.9(3) . . . . ?
C8 C9 C10 N1 1.2(5) . . . . ?
C8 C9 C10 C11 -179.4(3) . . . . ?
C9 C10 C11 C12 -178.5(3) . . . . ?
C10 N1 C18 C13 1.1(4) . . . . ?
C10 N1 C18 C17 -178.4(3) . . . . ?
C10 N1 B1 N2 -2.3(4) . . . . ?
C10 N1 B1 C19 110.4(3) . . . . ?
C10 N1 B1 C25 -115.4(3) . . . . ?
C10 C11 C12 C13 0.0(6) . . . . ?
C11 C12 C13 C14 179.0(4) . . . . ?
C11 C12 C13 C18 -0.3(6) . . . . ?
C12 C13 C14 C15 -178.6(5) . . . . ?
C12 C13 C18 N1 -0.3(5) . . . . ?
C12 C13 C18 C17 179.3(3) . . . . ?
C13 C14 C15 C16 -0.8(8) . . . . ?
C14 C13 C18 N1 -179.6(3) . . . . ?
C14 C13 C18 C17 0.0(5) . . . . ?
C14 C15 C16 C17 0.3(7) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
C16 C17 C18 N1 179.1(3) . . . . ?
C16 C17 C18 C13 -0.4(5) . . . . ?
C18 N1 C10 C9 178.0(3) . . . . ?
C18 N1 C10 C11 -1.4(4) . . . . ?
C18 N1 B1 N2 179.1(2) . . . . ?
C18 N1 B1 C19 -68.3(3) . . . . ?
C18 N1 B1 C25 65.9(3) . . . . ?
C18 C13 C14 C15 0.7(6) . . . . ?
C19 C20 C21 C22 -0.9(6) . . . . ?
C20 C19 C24 C23 0.5(6) . . . . ?
C20 C19 B1 N1 -49.2(4) . . . . ?
C20 C19 B1 N2 62.7(4) . . . . ?
C20 C19 B1 C25 -175.1(3) . . . . ?
C20 C21 C22 C23 1.9(6) . . . . ?
C21 C22 C23 C24 -1.7(7) . . . . ?
C22 C23 C24 C19 0.5(8) . . . . ?
C24 C19 C20 C21 -0.4(5) . . . . ?
C24 C19 B1 N1 134.8(4) . . . . ?
C24 C19 B1 N2 -113.3(4) . . . . ?
C24 C19 B1 C25 9.0(5) . . . . ?
C25 C26 C27 C28 -1.8(8) . . . . ?
C26 C25 C30 C29 -1.3(5) . . . . ?
C26 C25 B1 N1 -123.2(4) . . . . ?
C26 C25 B1 N2 124.4(4) . . . . ?
C26 C25 B1 C19 2.2(5) . . . . ?
C26 C27 C28 C29 -0.2(8) . . . . ?
C27 C28 C29 C30 1.2(7) . . . . ?
C28 C29 C30 C25 -0.4(6) . . . . ?
C30 C25 C26 C27 2.4(6) . . . . ?
C30 C25 B1 N1 59.9(4) . . . . ?
C30 C25 B1 N2 -52.5(4) . . . . ?
C30 C25 B1 C19 -174.7(3) . . . . ?
B1 N1 C10 C9 -0.7(4) . . . . ?
B1 N1 C10 C11 179.9(3) . . . . ?
B1 N1 C18 C13 179.8(3) . . . . ?
B1 N1 C18 C17 0.3(4) . . . . ?
B1 N2 C1 C2 5.4(5) . . . . ?
B1 N2 C1 C6 -175.7(3) . . . . ?
B1 N2 C8 C7 175.1(3) . . . . ?
B1 N2 C8 C9 -5.9(5) . . . . ?
B1 C19 C20 C21 -176.9(3) . . . . ?
B1 C19 C24 C23 176.7(4) . . . . ?
B1 C25 C26 C27 -174.7(4) . . . . ?
B1 C25 C30 C29 176.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
