# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mi20009_refinalized
_database_code_depnum_ccdc_archive 'CCDC 2051058'
loop_
_audit_author_name
_audit_author_address
'Jurgen Pahl'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;
_audit_creation_date             2020-10-16
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 B Cl2 N2 O'
_chemical_formula_sum            'C15 H9 B Cl2 N2 O'
_chemical_formula_weight         314.95
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H9 B1 Cl2 N2 O1'
_chemical_oxdiff_usercomment     '@ 120 K SI-222'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.2660(2)
_cell_length_b                   11.4559(3)
_cell_length_c                   12.8747(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1366.65(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5822
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.4590
_cell_measurement_theta_min      5.1140
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.287
_exptl_absorpt_coefficient_mu    4.252
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0165
-1 0 1 0.0148
2 0 1 0.0216
-2 0 -1 0.0199
0 -1 0 0.1923
0 1 0 0.1996
0 0 1 0.0244
0 0 -1 0.0155

_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.031
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 0.0000 -1.0000 -0.2023 0.0176 -0.0265
-1.0000 -0.0000 1.0000 0.2023 -0.0176 0.0265
2.0000 -0.0000 1.0000 -0.2328 -0.2596 0.0585
-2.0000 0.0000 -1.0000 0.2328 0.2596 -0.0585
-0.0000 -1.0000 -0.0000 -0.0133 0.0405 0.1275
0.0000 1.0000 0.0000 0.0133 -0.0405 -0.1275
-0.0000 -0.0000 1.0000 0.0573 -0.0982 0.0372
0.0000 0.0000 -1.0000 -0.0573 0.0982 -0.0372

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14822
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.297
_diffrn_reflns_theta_min         5.168
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  15.00   1.00   15.00    --  -38.34 100.00 173.00   97
  2  ω      6.00  83.00   1.00   15.00    --   38.34-100.00  67.00   77
  3  ω    104.00 178.00   1.00   30.00    --  116.00 100.00 173.00   74
  4  ω     31.00 107.00   1.00   30.00    --  116.00-100.00  67.00   76
  5  ω   -116.00  -6.00   1.00   15.00    --  -38.34 -57.00 -60.00  110
  6  ω    -40.00  71.00   1.00   15.00    --   38.34 -57.00-180.00  111
  7  ω    -21.00  74.00   1.00   15.00    --   38.34 -77.00 -90.00   95
  8  ω     38.00 149.00   1.00   30.00    --  116.00 -61.00  60.00  111
  9  ω     29.00 107.00   1.00   30.00    --  116.00 -94.00  90.00   78
 10  ω     61.00 146.00   1.00   30.00    --  116.00 178.00  90.00   85
 11  ω     35.00 109.00   1.00   30.00    --  116.00-111.00 -60.00   74
 12  ω    103.00 178.00   1.00   30.00    --  116.00  77.00 -30.00   75
 13  ω     29.00 107.00   1.00   30.00    --  116.00 -94.00 -60.00   78
 14  ω     83.00 178.00   1.00   30.00    --  116.00  61.00  30.00   95
 15  ω     38.00 149.00   1.00   30.00    --  116.00 -61.00-150.00  111
 16  ω     35.00 178.00   1.00   30.00    --  116.00  15.00   0.00  143
 17  ω   -116.00  -6.00   1.00   15.00    --  -38.34 -57.00  60.00  110
 18  ω   -116.00  -6.00   1.00   15.00    --  -38.34 -57.00-180.00  110
 19  ω   -116.00  -6.00   1.00   15.00    --  -38.34 -57.00 120.00  110
 20  ω   -118.00  -7.00   1.00   15.00    --  -38.34 -38.00 -30.00  111
 21  ω   -126.00 -37.00   1.00   15.00    --  -38.34 178.00-120.00   89
 22  ω    -70.00  41.00   1.00   15.00    --  -38.34  38.00  90.00  111
 23  ω     78.00 152.00   1.00   30.00    --  116.00  30.00 120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1450553000
_diffrn_orient_matrix_UB_12      0.0132912000
_diffrn_orient_matrix_UB_13      0.0572648000
_diffrn_orient_matrix_UB_21      -0.0806688000
_diffrn_orient_matrix_UB_22      -0.0404600000
_diffrn_orient_matrix_UB_23      -0.0982300000
_diffrn_orient_matrix_UB_31      0.0106872000
_diffrn_orient_matrix_UB_32      -0.1275420000
_diffrn_orient_matrix_UB_33      0.0371739000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2541
_reflns_number_total             2851
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 
;
 Flack x determined using 958 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.069
_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)+(0.0938P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1470
_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:
 C1(H1), C6(H6), C4(H4), C14(H14), C5(H5), C2(H2), C11(H11), C13(H13), C12(H12)
;
_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
Cl2 Cl 0.51375(15) 0.34822(10) 0.72962(11) 0.0421(3) Uani 1 1 d . . . . .
Cl1 Cl 0.29306(12) 0.54615(13) 0.74272(11) 0.0473(4) Uani 1 1 d . . . . .
O1 O 0.7601(3) 0.6996(3) 0.6446(2) 0.0282(7) Uani 1 1 d . . . . .
N2 N 0.5823(4) 0.5795(3) 0.6912(3) 0.0268(8) Uani 1 1 d . . . . .
N1 N 0.7377(4) 0.6534(3) 0.8190(3) 0.0283(8) Uani 1 1 d . . . . .
C9 C 0.6935(4) 0.6436(4) 0.7208(3) 0.0251(8) Uani 1 1 d . . . . .
C8 C 0.6546(5) 0.6009(4) 0.8979(3) 0.0280(9) Uani 1 1 d . . . . .
C15 C 0.5736(5) 0.5959(4) 0.5822(4) 0.0312(10) Uani 1 1 d . . . . .
C7 C 0.5349(5) 0.5309(4) 0.8814(4) 0.0299(9) Uani 1 1 d . . . . .
C10 C 0.6827(5) 0.6692(4) 0.5544(3) 0.0302(9) Uani 1 1 d . . . . .
C3 C 0.7135(6) 0.6361(4) 0.9926(4) 0.0333(10) Uani 1 1 d . . . . .
C1 C 0.8437(5) 0.7233(4) 0.8643(4) 0.0338(10) Uani 1 1 d . . . . .
H1 H 0.910869 0.768783 0.829095 0.041 Uiso 1 1 calc R . . . .
C6 C 0.4736(6) 0.4900(4) 0.9735(4) 0.0375(11) Uani 1 1 d . . . . .
H6 H 0.393389 0.441362 0.970111 0.045 Uiso 1 1 calc R . . . .
C4 C 0.6482(6) 0.5914(5) 1.0837(4) 0.0372(11) Uani 1 1 d . . . . .
H4 H 0.683764 0.609483 1.149317 0.045 Uiso 1 1 calc R . . . .
C14 C 0.4796(6) 0.5488(4) 0.5068(4) 0.0388(11) Uani 1 1 d . . . . .
H14 H 0.405891 0.496939 0.523339 0.047 Uiso 1 1 calc R . . . .
C5 C 0.5298(6) 0.5203(5) 1.0712(4) 0.0425(13) Uani 1 1 d . . . . .
H5 H 0.484881 0.490844 1.130273 0.051 Uiso 1 1 calc R . . . .
C2 C 0.8313(6) 0.7131(4) 0.9689(4) 0.0373(11) Uani 1 1 d . . . . .
H2 H 0.889795 0.750071 1.017545 0.045 Uiso 1 1 calc R . . . .
C11 C 0.7121(6) 0.7060(4) 0.4552(4) 0.0368(11) Uani 1 1 d . . . . .
H11 H 0.788779 0.755111 0.438893 0.044 Uiso 1 1 calc R . . . .
C13 C 0.5059(6) 0.5864(5) 0.4057(4) 0.0444(13) Uani 1 1 d . . . . .
H13 H 0.447006 0.558860 0.352610 0.053 Uiso 1 1 calc R . . . .
C12 C 0.6162(6) 0.6628(5) 0.3811(4) 0.0433(13) Uani 1 1 d . . . . .
H12 H 0.626726 0.686437 0.312426 0.052 Uiso 1 1 calc R . . . .
B1 B 0.4850(5) 0.5054(4) 0.7650(4) 0.0294(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
Cl2 B1 1.876(5) . ?
Cl1 B1 1.861(5) . ?
O1 C9 1.325(5) . ?
O1 C10 1.409(5) . ?
N2 C9 1.321(6) . ?
N2 C15 1.418(6) . ?
N2 B1 1.560(6) . ?
N1 C9 1.333(6) . ?
N1 C8 1.410(5) . ?
N1 C1 1.395(6) . ?
C8 C7 1.385(7) . ?
C8 C3 1.395(6) . ?
C15 C10 1.362(7) . ?
C15 C14 1.412(6) . ?
C7 C6 1.396(6) . ?
C7 B1 1.595(7) . ?
C10 C11 1.372(6) . ?
C3 C4 1.416(6) . ?
C3 C2 1.436(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.357(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.405(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.392(8) . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.394(7) . ?
C13 H13 0.9300 . ?
C13 C12 1.382(8) . ?
C12 H12 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
C9 O1 C10 104.7(3) . . ?
C9 N2 C15 104.8(4) . . ?
C9 N2 B1 125.3(4) . . ?
C15 N2 B1 129.9(4) . . ?
C9 N1 C8 118.7(4) . . ?
C9 N1 C1 131.4(4) . . ?
C1 N1 C8 109.1(4) . . ?
O1 C9 N1 121.2(4) . . ?
N2 C9 O1 114.8(4) . . ?
N2 C9 N1 124.0(4) . . ?
C7 C8 N1 125.0(4) . . ?
C7 C8 C3 128.0(4) . . ?
C3 C8 N1 107.0(4) . . ?
C10 C15 N2 107.5(4) . . ?
C10 C15 C14 120.8(5) . . ?
C14 C15 N2 131.7(5) . . ?
C8 C7 C6 112.9(4) . . ?
C8 C7 B1 118.8(4) . . ?
C6 C7 B1 128.2(4) . . ?
C15 C10 O1 108.2(4) . . ?
C15 C10 C11 125.6(4) . . ?
C11 C10 O1 126.2(4) . . ?
C8 C3 C4 116.9(5) . . ?
C8 C3 C2 106.8(4) . . ?
C4 C3 C2 136.3(5) . . ?
N1 C1 H1 126.1 . . ?
C2 C1 N1 107.9(4) . . ?
C2 C1 H1 126.1 . . ?
C7 C6 H6 119.1 . . ?
C7 C6 C5 121.8(5) . . ?
C5 C6 H6 119.1 . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.3(5) . . ?
C5 C4 H4 121.4 . . ?
C15 C14 H14 122.7 . . ?
C13 C14 C15 114.6(5) . . ?
C13 C14 H14 122.7 . . ?
C6 C5 H5 118.4 . . ?
C4 C5 C6 123.1(4) . . ?
C4 C5 H5 118.4 . . ?
C3 C2 H2 125.4 . . ?
C1 C2 C3 109.1(4) . . ?
C1 C2 H2 125.4 . . ?
C10 C11 H11 123.2 . . ?
C10 C11 C12 113.6(5) . . ?
C12 C11 H11 123.2 . . ?
C14 C13 H13 118.7 . . ?
C12 C13 C14 122.6(5) . . ?
C12 C13 H13 118.7 . . ?
C11 C12 H12 118.7 . . ?
C13 C12 C11 122.6(5) . . ?
C13 C12 H12 118.7 . . ?
Cl1 B1 Cl2 109.8(3) . . ?
N2 B1 Cl2 107.0(3) . . ?
N2 B1 Cl1 108.8(3) . . ?
N2 B1 C7 107.7(4) . . ?
C7 B1 Cl2 111.2(3) . . ?
C7 B1 Cl1 112.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.571
_oxdiff_exptl_absorpt_empirical_full_min 0.682
####################################################################### 
# 
# 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_mo_mi20014_0m
_database_code_depnum_ccdc_archive 'CCDC 2051059'
loop_
_audit_author_name
_audit_author_address
'Jurgen Pahl'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;
_audit_creation_date             2020-10-16
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 B Cl2 N2'
_chemical_formula_sum            'C13 H9 B Cl2 N2'
_chemical_formula_weight         274.93
_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'
Cl Cl 0.1484 0.1585 '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                   7.2198(4)
_cell_length_b                   8.3969(5)
_cell_length_c                   19.8689(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.203(2)
_cell_angle_gamma                90
_cell_volume                     1195.02(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8155
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.433
_cell_measurement_theta_min      2.636
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1302 before and 0.0706 after correction. The Ratio of minimum to maximum transmission is 0.7791. 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    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.453
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.076
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.527
_diffrn_reflns_theta_min         2.637
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3128
_reflns_number_total             3636
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.060
_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)+(0.0388P)²+0.4860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0928
_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:
 C10(H10), C12(H12), C7(H7), C13(H13), C11(H11), C4(H4), C2(H2), C6(H6), C5(H5)
;
_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
Cl1 Cl 0.38556(5) 0.16422(4) 0.36185(2) 0.02130(9) Uani 1 1 d . . . . .
Cl2 Cl 0.76215(5) 0.20628(4) 0.31198(2) 0.02034(9) Uani 1 1 d . . . . .
N2 N 0.59692(15) 0.44471(13) 0.38434(5) 0.0149(2) Uani 1 1 d . . . . .
N1 N 0.75082(15) 0.38054(13) 0.48535(5) 0.0146(2) Uani 1 1 d . . . . .
C9 C 0.67367(17) 0.50305(16) 0.44530(6) 0.0141(2) Uani 1 1 d . . . . .
C8 C 0.84348(17) 0.36549(16) 0.55110(6) 0.0144(2) Uani 1 1 d . . . . .
C10 C 0.66499(18) 0.66386(16) 0.46061(7) 0.0164(2) Uani 1 1 d . . . . .
H10 H 0.717743 0.704085 0.503456 0.020 Uiso 1 1 calc R . . . .
C12 C 0.50170(19) 0.70378(17) 0.34809(7) 0.0182(3) Uani 1 1 d . . . . .
H12 H 0.443415 0.773021 0.314001 0.022 Uiso 1 1 calc R . . . .
C3 C 0.87377(18) 0.20055(16) 0.56124(7) 0.0160(2) Uani 1 1 d . . . . .
C1 C 0.72382(18) 0.22955(16) 0.45443(7) 0.0156(2) Uani 1 1 d . . . . .
C7 C 0.90177(18) 0.47787(17) 0.60085(6) 0.0173(3) Uani 1 1 d . . . . .
H7 H 0.882208 0.588633 0.593225 0.021 Uiso 1 1 calc R . . . .
C13 C 0.51358(18) 0.54337(17) 0.33612(7) 0.0169(2) Uani 1 1 d . . . . .
H13 H 0.462572 0.501292 0.293403 0.020 Uiso 1 1 calc R . . . .
C11 C 0.57676(18) 0.76339(16) 0.41123(7) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.567066 0.873913 0.420397 0.022 Uiso 1 1 calc R . . . .
C4 C 0.96304(19) 0.14630(17) 0.62366(7) 0.0189(3) Uani 1 1 d . . . . .
H4 H 0.984129 0.035836 0.631610 0.023 Uiso 1 1 calc R . . . .
C2 C 0.79876(18) 0.11879(17) 0.49995(7) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.801243 0.007045 0.492638 0.021 Uiso 1 1 calc R . . . .
C6 C 0.98998(19) 0.42002(18) 0.66219(7) 0.0193(3) Uani 1 1 d . . . . .
H6 H 1.031102 0.493159 0.697399 0.023 Uiso 1 1 calc R . . . .
C5 C 1.01983(19) 0.25718(18) 0.67351(7) 0.0200(3) Uani 1 1 d . . . . .
H5 H 1.080166 0.222053 0.716164 0.024 Uiso 1 1 calc R . . . .
B1 B 0.6199(2) 0.25694(18) 0.38009(8) 0.0165(3) 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
Cl1 B1 1.8566(15) . ?
Cl2 B1 1.8480(16) . ?
N2 C9 1.3585(16) . ?
N2 C13 1.3497(16) . ?
N2 B1 1.5888(19) . ?
N1 C9 1.3749(16) . ?
N1 C8 1.3969(16) . ?
N1 C1 1.4116(16) . ?
C9 C10 1.3873(18) . ?
C8 C3 1.4126(19) . ?
C8 C7 1.3929(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3821(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3723(19) . ?
C12 C11 1.3955(19) . ?
C3 C4 1.4003(18) . ?
C3 C2 1.4429(18) . ?
C1 C2 1.3613(18) . ?
C1 B1 1.5874(19) . ?
C7 H7 0.9500 . ?
C7 C6 1.3902(18) . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.398(2) . ?
C5 H5 0.9500 . ?

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
C9 N2 B1 111.82(10) . . ?
C13 N2 C9 120.48(12) . . ?
C13 N2 B1 127.70(11) . . ?
C9 N1 C8 136.11(11) . . ?
C9 N1 C1 113.35(11) . . ?
C8 N1 C1 110.46(11) . . ?
N2 C9 N1 109.66(11) . . ?
N2 C9 C10 121.46(12) . . ?
N1 C9 C10 128.87(12) . . ?
N1 C8 C3 105.63(11) . . ?
C7 C8 N1 131.99(12) . . ?
C7 C8 C3 122.38(12) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 C9 117.54(12) . . ?
C11 C10 H10 121.2 . . ?
C13 C12 H12 120.6 . . ?
C13 C12 C11 118.83(13) . . ?
C11 C12 H12 120.6 . . ?
C8 C3 C2 108.13(11) . . ?
C4 C3 C8 119.41(12) . . ?
C4 C3 C2 132.46(13) . . ?
N1 C1 B1 107.35(11) . . ?
C2 C1 N1 107.63(11) . . ?
C2 C1 B1 145.02(12) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 C8 116.73(13) . . ?
C6 C7 H7 121.6 . . ?
N2 C13 C12 120.75(12) . . ?
N2 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C10 C11 C12 120.91(13) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.51(13) . . ?
C5 C4 H4 120.7 . . ?
C3 C2 H2 125.9 . . ?
C1 C2 C3 108.15(12) . . ?
C1 C2 H2 125.9 . . ?
C7 C6 H6 119.1 . . ?
C7 C6 C5 121.81(13) . . ?
C5 C6 H6 119.1 . . ?
C4 C5 C6 121.15(12) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
Cl2 B1 Cl1 109.70(8) . . ?
N2 B1 Cl1 109.13(9) . . ?
N2 B1 Cl2 109.81(10) . . ?
C1 B1 Cl1 115.70(10) . . ?
C1 B1 Cl2 114.02(10) . . ?
C1 B1 N2 97.74(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
