# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_hy5783_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2cxy7h
_database_code_depnum_ccdc_archive 'CCDC 2202557'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;Fuzhou University
China
;
_audit_update_record             
;
2022-08-29 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-08-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 B N2 O2'
_chemical_formula_sum            'C18 H16 B N2 O2'
_chemical_formula_weight         303.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.822(4)
_cell_length_b                   9.698(8)
_cell_length_c                   17.608(14)
_cell_angle_alpha                84.39(4)
_cell_angle_beta                 83.54(4)
_cell_angle_gamma                49.04(3)
_cell_volume                     745.7(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2130
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.514
_cell_measurement_theta_min      2.328
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.6233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1279 before and 0.0805 after correction.
The Ratio of minimum to maximum transmission is 0.8344.
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    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12828
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.329
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1564
_reflns_number_total             2614
_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         0.294
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.028
_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)+(0.0983P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1873
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), N4(H4), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00M(H00E,H00G,H00M)
;
_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
O001 O 0.2504(5) 0.7207(3) 0.51149(11) 0.0534(7) Uani 1 1 d . . . . .
O2 O 0.5493(4) 0.8474(3) 0.08465(10) 0.0524(6) Uani 1 1 d . . . . .
N003 N 0.4164(5) 0.6660(3) 0.67096(12) 0.0386(6) Uani 1 1 d . . . . .
H003 H 0.339721 0.620883 0.658098 0.046 Uiso 1 1 calc R U . . .
N4 N 0.2355(6) 0.7327(4) 0.43210(13) 0.0545(8) Uani 1 1 d . . . . .
H4 H 0.117989 0.730483 0.407709 0.065 Uiso 1 1 calc R U . . .
C005 C 0.4362(6) 0.6702(4) 0.74830(15) 0.0335(7) Uani 1 1 d . . . . .
C006 C 0.5555(6) 0.7478(4) 0.77056(15) 0.0330(7) Uani 1 1 d . . . . .
C007 C 0.4697(6) 0.7685(4) 0.31909(15) 0.0345(7) Uani 1 1 d . . . . .
C008 C 0.7460(6) 0.7108(4) 0.28464(16) 0.0385(7) Uani 1 1 d . . . . .
H008 H 0.909585 0.655694 0.314740 0.046 Uiso 1 1 calc R U . . .
C009 C 0.4328(6) 0.7478(4) 0.40222(16) 0.0366(7) Uani 1 1 d . . . . .
C00A C 0.2276(6) 0.8512(4) 0.27275(16) 0.0378(7) Uani 1 1 d . . . . .
H00A H 0.040887 0.890415 0.294419 0.045 Uiso 1 1 calc R U . . .
C00B C 0.2619(6) 0.8754(4) 0.19574(16) 0.0405(8) Uani 1 1 d . . . . .
H00B H 0.097786 0.931957 0.165633 0.049 Uiso 1 1 calc R U . . .
C00C C 0.3414(6) 0.6010(4) 0.80358(16) 0.0398(7) Uani 1 1 d . . . . .
H00C H 0.267069 0.547837 0.788810 0.048 Uiso 1 1 calc R U . . .
C00D C 0.7832(6) 0.7332(4) 0.20708(16) 0.0396(7) Uani 1 1 d . . . . .
H00D H 0.970214 0.693017 0.185191 0.048 Uiso 1 1 calc R U . . .
C00E C 0.4645(6) 0.7308(4) 0.52748(16) 0.0404(7) Uani 1 1 d . . . . .
C00F C 0.6633(6) 0.8128(4) 0.71333(16) 0.0399(7) Uani 1 1 d . . . . .
H00F H 0.743235 0.862100 0.728794 0.048 Uiso 1 1 calc R U . . .
C00G C 0.5407(6) 0.8159(4) 0.16200(15) 0.0375(7) Uani 1 1 d . . . . .
C00H C 0.6527(6) 0.8049(4) 0.63802(16) 0.0429(8) Uani 1 1 d . . . . .
H00H H 0.730021 0.844776 0.602281 0.051 Uiso 1 1 calc R U . . .
C00I C 0.5838(6) 0.7460(4) 0.46056(15) 0.0412(8) Uani 1 1 d . . . . .
H00I H 0.735736 0.753746 0.453876 0.049 Uiso 1 1 calc R U . . .
C00J C 0.5647(6) 0.7565(4) 0.84861(16) 0.0430(8) Uani 1 1 d . . . . .
H00J H 0.640025 0.808301 0.864343 0.052 Uiso 1 1 calc R U . . .
C00K C 0.3571(6) 0.6111(4) 0.87954(17) 0.0477(8) Uani 1 1 d . . . . .
H00K H 0.294213 0.563932 0.916044 0.057 Uiso 1 1 calc R U . . .
C00L C 0.4663(7) 0.6911(4) 0.90287(17) 0.0494(9) Uani 1 1 d . . . . .
H00L H 0.472226 0.699999 0.954603 0.059 Uiso 1 1 calc R U . . .
C00M C 0.8264(7) 0.7938(5) 0.04792(17) 0.0637(10) Uani 1 1 d . . . . .
H00E H 0.800017 0.827183 -0.005520 0.096 Uiso 1 1 calc R U . . .
H00G H 0.984937 0.663938 0.053969 0.096 Uiso 1 1 calc R U . . .
H00M H 0.881139 0.854155 0.070534 0.096 Uiso 1 1 calc R U . . .
B1 B 0.5130(7) 0.7303(5) 0.61180(18) 0.0385(8) 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
O001 N4 1.399(3) . ?
O001 C00E 1.374(3) . ?
O2 C00G 1.369(3) . ?
O2 C00M 1.422(4) . ?
N003 H003 0.8600 . ?
N003 C005 1.386(3) . ?
N003 B1 1.411(4) . ?
N4 H4 0.8600 . ?
N4 C009 1.299(3) . ?
C005 C006 1.417(4) . ?
C005 C00C 1.392(4) . ?
C006 C00F 1.435(4) . ?
C006 C00J 1.394(4) . ?
C007 C008 1.391(4) . ?
C007 C009 1.469(4) . ?
C007 C00A 1.395(4) . ?
C008 H008 0.9300 . ?
C008 C00D 1.377(4) . ?
C009 C00I 1.417(4) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.368(4) . ?
C00B H00B 0.9300 . ?
C00B C00G 1.394(4) . ?
C00C H00C 0.9300 . ?
C00C C00K 1.368(4) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.382(4) . ?
C00E C00I 1.345(4) . ?
C00E B1 1.541(4) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.346(4) . ?
C00H H00H 0.9300 . ?
C00H B1 1.523(4) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00L 1.371(4) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.394(4) . ?
C00L H00L 0.9300 . ?
C00M H00E 0.9600 . ?
C00M H00G 0.9600 . ?
C00M H00M 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00E O001 N4 108.5(2) . . ?
C00G O2 C00M 117.8(2) . . ?
C005 N003 H003 117.6 . . ?
C005 N003 B1 124.7(2) . . ?
B1 N003 H003 117.6 . . ?
O001 N4 H4 126.5 . . ?
C009 N4 O001 107.0(2) . . ?
C009 N4 H4 126.5 . . ?
N003 C005 C006 118.4(2) . . ?
N003 C005 C00C 121.6(3) . . ?
C00C C005 C006 120.0(3) . . ?
C005 C006 C00F 119.8(2) . . ?
C00J C006 C005 117.7(3) . . ?
C00J C006 C00F 122.4(3) . . ?
C008 C007 C009 120.7(2) . . ?
C008 C007 C00A 118.1(3) . . ?
C00A C007 C009 121.2(2) . . ?
C007 C008 H008 119.2 . . ?
C00D C008 C007 121.6(3) . . ?
C00D C008 H008 119.2 . . ?
N4 C009 C007 121.1(2) . . ?
N4 C009 C00I 110.2(3) . . ?
C00I C009 C007 128.7(3) . . ?
C007 C00A H00A 119.7 . . ?
C00B C00A C007 120.6(3) . . ?
C00B C00A H00A 119.7 . . ?
C00A C00B H00B 119.7 . . ?
C00A C00B C00G 120.6(3) . . ?
C00G C00B H00B 119.7 . . ?
C005 C00C H00C 119.9 . . ?
C00K C00C C005 120.2(3) . . ?
C00K C00C H00C 119.9 . . ?
C008 C00D H00D 120.2 . . ?
C008 C00D C00G 119.6(3) . . ?
C00G C00D H00D 120.2 . . ?
O001 C00E B1 118.6(2) . . ?
C00I C00E O001 107.7(2) . . ?
C00I C00E B1 133.6(3) . . ?
C006 C00F H00F 118.9 . . ?
C00H C00F C006 122.3(3) . . ?
C00H C00F H00F 118.9 . . ?
O2 C00G C00B 115.7(2) . . ?
O2 C00G C00D 124.8(3) . . ?
C00D C00G C00B 119.5(3) . . ?
C00F C00H H00H 120.2 . . ?
C00F C00H B1 119.5(3) . . ?
B1 C00H H00H 120.2 . . ?
C009 C00I H00I 126.7 . . ?
C00E C00I C009 106.6(3) . . ?
C00E C00I H00I 126.7 . . ?
C006 C00J H00J 119.0 . . ?
C00L C00J C006 122.1(3) . . ?
C00L C00J H00J 119.0 . . ?
C00C C00K H00K 119.6 . . ?
C00C C00K C00L 120.8(3) . . ?
C00L C00K H00K 119.6 . . ?
C00J C00L C00K 119.2(3) . . ?
C00J C00L H00L 120.4 . . ?
C00K C00L H00L 120.4 . . ?
O2 C00M H00E 109.5 . . ?
O2 C00M H00G 109.5 . . ?
O2 C00M H00M 109.5 . . ?
H00E C00M H00G 109.5 . . ?
H00E C00M H00M 109.5 . . ?
H00G C00M H00M 109.5 . . ?
N003 B1 C00E 121.2(3) . . ?
N003 B1 C00H 115.2(3) . . ?
C00H B1 C00E 123.6(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
O001 N4 C009 C007 -178.3(2) . . . . ?
O001 N4 C009 C00I 0.1(3) . . . . ?
O001 C00E C00I C009 0.9(3) . . . . ?
O001 C00E B1 N003 19.3(4) . . . . ?
O001 C00E B1 C00H -158.0(3) . . . . ?
N003 C005 C006 C00F -2.5(4) . . . . ?
N003 C005 C006 C00J 177.9(2) . . . . ?
N003 C005 C00C C00K -178.4(2) . . . . ?
N4 O001 C00E C00I -0.9(3) . . . . ?
N4 O001 C00E B1 177.0(2) . . . . ?
N4 C009 C00I C00E -0.6(3) . . . . ?
C005 N003 B1 C00E -176.3(2) . . . . ?
C005 N003 B1 C00H 1.2(4) . . . . ?
C005 C006 C00F C00H 0.8(4) . . . . ?
C005 C006 C00J C00L 0.8(4) . . . . ?
C005 C00C C00K C00L 0.3(4) . . . . ?
C006 C005 C00C C00K 1.3(4) . . . . ?
C006 C00F C00H B1 2.0(4) . . . . ?
C006 C00J C00L C00K 0.9(4) . . . . ?
C007 C008 C00D C00G 0.4(4) . . . . ?
C007 C009 C00I C00E 177.6(3) . . . . ?
C007 C00A C00B C00G 0.7(4) . . . . ?
C008 C007 C009 N4 -153.3(3) . . . . ?
C008 C007 C009 C00I 28.7(5) . . . . ?
C008 C007 C00A C00B -0.3(4) . . . . ?
C008 C00D C00G O2 179.3(3) . . . . ?
C008 C00D C00G C00B 0.0(4) . . . . ?
C009 C007 C008 C00D -178.3(3) . . . . ?
C009 C007 C00A C00B 177.7(2) . . . . ?
C00A C007 C008 C00D -0.2(4) . . . . ?
C00A C007 C009 N4 28.7(4) . . . . ?
C00A C007 C009 C00I -149.3(3) . . . . ?
C00A C00B C00G O2 -179.9(2) . . . . ?
C00A C00B C00G C00D -0.5(4) . . . . ?
C00C C005 C006 C00F 177.7(2) . . . . ?
C00C C005 C006 C00J -1.9(4) . . . . ?
C00C C00K C00L C00J -1.4(4) . . . . ?
C00E O001 N4 C009 0.5(3) . . . . ?
C00F C006 C00J C00L -178.8(3) . . . . ?
C00F C00H B1 N003 -2.9(4) . . . . ?
C00F C00H B1 C00E 174.5(3) . . . . ?
C00I C00E B1 N003 -163.5(3) . . . . ?
C00I C00E B1 C00H 19.2(5) . . . . ?
C00J C006 C00F C00H -179.7(3) . . . . ?
C00M O2 C00G C00B 178.3(3) . . . . ?
C00M O2 C00G C00D -1.0(4) . . . . ?
B1 N003 C005 C006 1.4(4) . . . . ?
B1 N003 C005 C00C -178.8(3) . . . . ?
B1 C00E C00I C009 -176.5(3) . . . . ?

_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 
# 
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data_hy-578
_audit_block_doi                 10.5517/ccdc.csd.cc2cxy8j
_database_code_depnum_ccdc_archive 'CCDC 2202558'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;Fuzhou University
China
;
_audit_update_record             
;
2022-08-20 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 B Br Cl N2 O'
_chemical_formula_weight         385.45

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0910(6)
_cell_length_b                   17.1679(11)
_cell_length_c                   10.8642(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.897(2)
_cell_angle_gamma                90
_cell_volume                     1630.76(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    205
_cell_measurement_theta_min      4.74
_cell_measurement_theta_max      20.94

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.688
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22664
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.282
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2860
_reflns_number_gt                2353
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+1.8968P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0111(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2860
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br Br 0.30964(6) 0.21498(3) 0.74717(5) 0.0814(3) Uani 1 1 d . . . . .
Cl00 Cl 0.53872(19) 0.42105(8) 1.13600(11) 0.0953(5) Uani 1 1 d . . . . .
O003 O 0.6041(4) 0.21313(19) 0.4879(3) 0.0774(10) Uani 1 1 d . . . . .
N004 N 0.2539(4) 0.40030(18) 0.3637(3) 0.0507(8) Uani 1 1 d . . . . .
H004 H 0.249977 0.364983 0.306713 0.061 Uiso 1 1 calc R U . . .
C005 C 0.5621(4) 0.3158(2) 0.7624(3) 0.0440(8) Uani 1 1 d . . . . .
C006 C 0.5570(4) 0.2875(2) 0.6325(4) 0.0467(9) Uani 1 1 d . . . . .
N6 N 0.6389(5) 0.2267(2) 0.6210(4) 0.0639(9) Uani 1 1 d . . . . .
C008 C 0.4542(4) 0.2918(2) 0.8227(4) 0.0483(9) Uani 1 1 d . . . . .
C009 C 0.4665(5) 0.3174(2) 0.5125(4) 0.0496(9) Uani 1 1 d . . . . .
C00A C 0.1571(4) 0.4638(2) 0.3305(4) 0.0486(9) Uani 1 1 d . . . . .
C00B C 0.1598(5) 0.5219(2) 0.4214(4) 0.0521(9) Uani 1 1 d . . . . .
C00C C 0.5521(5) 0.3785(2) 0.9944(4) 0.0591(11) Uani 1 1 d . . . . .
C00D C 0.6700(5) 0.3693(2) 0.8254(4) 0.0609(11) Uani 1 1 d . . . . .
H00D H 0.747338 0.384433 0.789494 0.073 Uiso 1 1 calc R U . . .
C00E C 0.3581(5) 0.4543(3) 0.5815(4) 0.0644(12) Uani 1 1 d . . . . .
H00E H 0.423678 0.451766 0.663831 0.077 Uiso 1 1 calc R U . . .
C00F C 0.0569(5) 0.4715(3) 0.2075(4) 0.0656(12) Uani 1 1 d . . . . .
H00F H 0.054647 0.433201 0.146387 0.079 Uiso 1 1 calc R U . . .
C00G C 0.4465(5) 0.3232(2) 0.9383(4) 0.0568(10) Uani 1 1 d . . . . .
H00G H 0.371760 0.307161 0.976544 0.068 Uiso 1 1 calc R U . . .
C00H C 0.2623(6) 0.5146(3) 0.5467(4) 0.0676(12) Uani 1 1 d . . . . .
H00H H 0.262586 0.553400 0.606544 0.081 Uiso 1 1 calc R U . . .
C00I C 0.5032(6) 0.2675(3) 0.4295(4) 0.0660(12) Uani 1 1 d . . . . .
H00I H 0.462755 0.270530 0.341199 0.079 Uiso 1 1 calc R U . . .
C00J C 0.6644(6) 0.4006(3) 0.9411(5) 0.0704(13) Uani 1 1 d . . . . .
H00J H 0.737425 0.436800 0.982453 0.084 Uiso 1 1 calc R U . . .
C00K C -0.0376(5) 0.5346(3) 0.1766(5) 0.0711(13) Uani 1 1 d . . . . .
H00K H -0.102576 0.539148 0.094325 0.085 Uiso 1 1 calc R U . . .
C00L C 0.0591(5) 0.5855(3) 0.3864(5) 0.0664(12) Uani 1 1 d . . . . .
H00L H 0.058421 0.623968 0.446412 0.080 Uiso 1 1 calc R U . . .
C00M C -0.0376(5) 0.5917(3) 0.2660(5) 0.0687(13) Uani 1 1 d . . . . .
H00M H -0.103122 0.634139 0.244349 0.082 Uiso 1 1 calc R U . . .
B1 B 0.3590(5) 0.3900(3) 0.4857(4) 0.0501(10) 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
Br C008 1.884(4) . ?
Cl00 C00C 1.737(4) . ?
O003 C00I 1.341(6) . ?
O003 N6 1.412(5) . ?
N004 C00A 1.386(5) . ?
N004 B1 1.417(5) . ?
N004 H004 0.8600 . ?
C005 C00D 1.381(5) . ?
C005 C008 1.383(6) . ?
C005 C006 1.482(5) . ?
C006 N6 1.307(5) . ?
C006 C009 1.433(5) . ?
C008 C00G 1.385(5) . ?
C009 C00I 1.350(6) . ?
C009 B1 1.560(6) . ?
C00A C00B 1.399(5) . ?
C00A C00F 1.402(6) . ?
C00B C00L 1.408(6) . ?
C00B C00H 1.430(6) . ?
C00C C00J 1.359(7) . ?
C00C C00G 1.369(6) . ?
C00D C00J 1.380(7) . ?
C00D H00D 0.9300 . ?
C00E C00H 1.340(6) . ?
C00E B1 1.518(6) . ?
C00E H00E 0.9300 . ?
C00F C00K 1.366(6) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K C00M 1.380(7) . ?
C00K H00K 0.9300 . ?
C00L C00M 1.366(6) . ?
C00L H00L 0.9300 . ?
C00M H00M 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
C00I O003 N6 107.6(3) . . ?
C00A N004 B1 124.0(3) . . ?
C00A N004 H004 118.0 . . ?
B1 N004 H004 118.0 . . ?
C00D C005 C008 117.6(4) . . ?
C00D C005 C006 121.5(4) . . ?
C008 C005 C006 120.9(3) . . ?
N6 C006 C009 113.5(4) . . ?
N6 C006 C005 118.9(3) . . ?
C009 C006 C005 127.6(3) . . ?
C006 N6 O003 104.9(3) . . ?
C005 C008 C00G 122.2(4) . . ?
C005 C008 Br 120.2(3) . . ?
C00G C008 Br 117.7(3) . . ?
C00I C009 C006 101.2(3) . . ?
C00I C009 B1 129.7(4) . . ?
C006 C009 B1 129.0(3) . . ?
N004 C00A C00B 119.4(3) . . ?
N004 C00A C00F 121.5(4) . . ?
C00B C00A C00F 119.1(4) . . ?
C00A C00B C00L 118.5(4) . . ?
C00A C00B C00H 119.4(4) . . ?
C00L C00B C00H 122.1(4) . . ?
C00J C00C C00G 121.4(4) . . ?
C00J C00C Cl00 120.2(3) . . ?
C00G C00C Cl00 118.4(4) . . ?
C00J C00D C005 120.8(4) . . ?
C00J C00D H00D 119.6 . . ?
C005 C00D H00D 119.6 . . ?
C00H C00E B1 119.6(4) . . ?
C00H C00E H00E 120.2 . . ?
B1 C00E H00E 120.2 . . ?
C00K C00F C00A 120.6(4) . . ?
C00K C00F H00F 119.7 . . ?
C00A C00F H00F 119.7 . . ?
C00C C00G C008 118.0(4) . . ?
C00C C00G H00G 121.0 . . ?
C008 C00G H00G 121.0 . . ?
C00E C00H C00B 122.7(4) . . ?
C00E C00H H00H 118.6 . . ?
C00B C00H H00H 118.6 . . ?
O003 C00I C009 112.8(4) . . ?
O003 C00I H00I 123.6 . . ?
C009 C00I H00I 123.6 . . ?
C00C C00J C00D 119.9(4) . . ?
C00C C00J H00J 120.1 . . ?
C00D C00J H00J 120.1 . . ?
C00F C00K C00M 120.8(4) . . ?
C00F C00K H00K 119.6 . . ?
C00M C00K H00K 119.6 . . ?
C00M C00L C00B 121.3(4) . . ?
C00M C00L H00L 119.3 . . ?
C00B C00L H00L 119.3 . . ?
C00L C00M C00K 119.6(4) . . ?
C00L C00M H00M 120.2 . . ?
C00K C00M H00M 120.2 . . ?
N004 B1 C00E 114.9(4) . . ?
N004 B1 C009 120.1(4) . . ?
C00E B1 C009 125.0(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
C00D C005 C006 N6 88.5(5) . . . . ?
C008 C005 C006 N6 -94.3(5) . . . . ?
C00D C005 C006 C009 -93.9(5) . . . . ?
C008 C005 C006 C009 83.3(5) . . . . ?
C009 C006 N6 O003 -0.3(5) . . . . ?
C005 C006 N6 O003 177.6(3) . . . . ?
C00I O003 N6 C006 0.1(5) . . . . ?
C00D C005 C008 C00G 4.0(6) . . . . ?
C006 C005 C008 C00G -173.3(4) . . . . ?
C00D C005 C008 Br -176.7(3) . . . . ?
C006 C005 C008 Br 6.0(5) . . . . ?
N6 C006 C009 C00I 0.4(5) . . . . ?
C005 C006 C009 C00I -177.3(4) . . . . ?
N6 C006 C009 B1 -177.8(4) . . . . ?
C005 C006 C009 B1 4.5(7) . . . . ?
B1 N004 C00A C00B -0.6(6) . . . . ?
B1 N004 C00A C00F 179.1(4) . . . . ?
N004 C00A C00B C00L -179.1(4) . . . . ?
C00F C00A C00B C00L 1.2(6) . . . . ?
N004 C00A C00B C00H 0.0(6) . . . . ?
C00F C00A C00B C00H -179.7(4) . . . . ?
C008 C005 C00D C00J -3.5(6) . . . . ?
C006 C005 C00D C00J 173.8(4) . . . . ?
N004 C00A C00F C00K -179.9(4) . . . . ?
C00B C00A C00F C00K -0.2(6) . . . . ?
C00J C00C C00G C008 -2.0(6) . . . . ?
Cl00 C00C C00G C008 177.4(3) . . . . ?
C005 C008 C00G C00C -1.4(6) . . . . ?
Br C008 C00G C00C 179.4(3) . . . . ?
B1 C00E C00H C00B -0.4(8) . . . . ?
C00A C00B C00H C00E 0.5(7) . . . . ?
C00L C00B C00H C00E 179.6(5) . . . . ?
N6 O003 C00I C009 0.2(5) . . . . ?
C006 C009 C00I O003 -0.3(5) . . . . ?
B1 C009 C00I O003 177.8(4) . . . . ?
C00G C00C C00J C00D 2.5(7) . . . . ?
Cl00 C00C C00J C00D -176.9(3) . . . . ?
C005 C00D C00J C00C 0.3(7) . . . . ?
C00A C00F C00K C00M -0.7(7) . . . . ?
C00A C00B C00L C00M -1.2(7) . . . . ?
C00H C00B C00L C00M 179.7(5) . . . . ?
C00B C00L C00M C00K 0.2(7) . . . . ?
C00F C00K C00M C00L 0.7(7) . . . . ?
C00A N004 B1 C00E 0.6(6) . . . . ?
C00A N004 B1 C009 -178.3(4) . . . . ?
C00H C00E B1 N004 -0.1(7) . . . . ?
C00H C00E B1 C009 178.7(4) . . . . ?
C00I C009 B1 N004 16.3(7) . . . . ?
C006 C009 B1 N004 -166.1(4) . . . . ?
C00I C009 B1 C00E -162.5(5) . . . . ?
C006 C009 B1 C00E 15.1(7) . . . . ?

_refine_diff_density_max         1.228
_refine_diff_density_min         -1.065
_refine_diff_density_rms         0.080

