# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_liguoping20170512_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1818909'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 B Br2 N'
_chemical_formula_weight         531.08

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   11.2690(4)
_cell_length_b                   7.3358(3)
_cell_length_c                   14.2605(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.4180(10)
_cell_angle_gamma                90
_cell_volume                     1155.54(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.522
_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      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28928
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         26.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4728
_reflns_number_gt                4449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.8896P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4728
_refine_ls_number_parameters     283
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7105(3) 0.6376(4) 0.7167(2) 0.0177(6) Uani 1 1 d . . . . .
B1 B 0.6023(4) 0.6673(6) 0.7506(3) 0.0189(8) Uani 1 1 d . . . . .
Br1 Br 0.96526(4) 0.43484(6) 0.46153(3) 0.03606(12) Uani 1 1 d . . . . .
Br2 Br 0.14321(3) 0.44919(8) 0.74676(3) 0.03751(12) Uani 1 1 d . . . . .
C1 C 0.4926(3) 0.5477(5) 0.7049(3) 0.0191(7) Uani 1 1 d . . . . .
C2 C 0.3845(3) 0.5498(5) 0.7402(3) 0.0214(8) Uani 1 1 d . . . . .
H2 H 0.3767 0.6297 0.7911 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2897(3) 0.4366(8) 0.7014(2) 0.0245(7) Uani 1 1 d . . . . .
C4 C 0.2993(4) 0.3155(6) 0.6283(3) 0.0288(9) Uani 1 1 d . . . . .
H4 H 0.2337 0.2373 0.6025 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4049(4) 0.3101(6) 0.5937(3) 0.0274(9) Uani 1 1 d . . . . .
H5 H 0.4121 0.2260 0.5445 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5024(3) 0.4268(7) 0.6297(2) 0.0204(7) Uani 1 1 d . . . . .
C7 C 0.6135(3) 0.4274(7) 0.5909(2) 0.0206(7) Uani 1 1 d . . . . .
C8 C 0.6222(4) 0.3314(6) 0.5074(3) 0.0272(9) Uani 1 1 d . . . . .
H8 H 0.5539 0.2637 0.4759 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8223(4) 0.5262(5) 0.5982(3) 0.0224(8) Uani 1 1 d . . . . .
H9 H 0.8921 0.5909 0.6292 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7250(4) 0.3308(6) 0.4690(3) 0.0285(9) Uani 1 1 d . . . . .
H10 H 0.7278 0.2649 0.4121 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8246(3) 0.4293(7) 0.5158(2) 0.0255(7) Uani 1 1 d . . . . .
C12 C 0.7164(3) 0.5289(5) 0.6361(2) 0.0175(7) Uani 1 1 d . . . . .
C13 C 0.5065(3) 0.9559(7) 0.8046(3) 0.0267(8) Uani 1 1 d . . . . .
H13 H 0.4542 0.9544 0.7435 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5931(3) 0.8175(5) 0.8279(3) 0.0194(7) Uani 1 1 d . . . . .
C15 C 0.6666(4) 0.8245(6) 0.9191(3) 0.0253(8) Uani 1 1 d . . . . .
H15 H 0.7265 0.7333 0.9377 0.030 Uiso 1 1 calc R U . . .
C16 C 0.8523(3) 0.8971(5) 0.7363(3) 0.0222(8) Uani 1 1 d . . . . .
C17 C 0.7686(4) 1.0000(6) 0.6599(3) 0.0311(10) Uani 1 1 d . . . . .
H17A H 0.8089 1.1110 0.6440 0.047 Uiso 1 1 calc R U . . .
H17B H 0.6951 1.0330 0.6830 0.047 Uiso 1 1 calc R U . . .
H17C H 0.7470 0.9235 0.6027 0.047 Uiso 1 1 calc R U . . .
C18 C 0.8993(4) 0.6250(6) 0.8350(3) 0.0232(8) Uani 1 1 d . . . . .
C19 C 0.8231(3) 0.7225(5) 0.7636(3) 0.0193(7) Uani 1 1 d . . . . .
C20 C 0.8692(4) 0.4333(8) 0.8610(3) 0.0331(8) Uani 1 1 d . . . . .
H20A H 0.7901 0.4325 0.8798 0.050 Uiso 1 1 calc R U . . .
H20B H 0.9313 0.3898 0.9144 0.050 Uiso 1 1 calc R U . . .
H20C H 0.8667 0.3531 0.8057 0.050 Uiso 1 1 calc R U . . .
C21 C 0.9628(3) 0.9704(6) 0.7803(3) 0.0272(9) Uani 1 1 d . . . . .
H21 H 0.9851 1.0874 0.7611 0.033 Uiso 1 1 calc R U . . .
C22 C 1.0421(4) 0.8775(6) 0.8517(3) 0.0329(10) Uani 1 1 d . . . . .
C23 C 1.0074(4) 0.7084(6) 0.8796(3) 0.0306(10) Uani 1 1 d . . . . .
H23 H 1.0587 0.6468 0.9307 0.037 Uiso 1 1 calc R U . . .
C24 C 0.6535(3) 0.9624(8) 0.9831(3) 0.0329(10) Uani 1 1 d . . . . .
H24 H 0.7040 0.9635 1.0449 0.039 Uiso 1 1 calc R U . . .
C25 C 0.5681(4) 1.0975(6) 0.9580(3) 0.0340(10) Uani 1 1 d . . . . .
H25 H 0.5597 1.1916 1.0020 0.041 Uiso 1 1 calc R U . . .
C26 C 0.4948(4) 1.0943(6) 0.8678(3) 0.0340(10) Uani 1 1 d . . . . .
H26 H 0.4363 1.1875 0.8494 0.041 Uiso 1 1 calc R U . . .
C27 C 1.1650(4) 0.9548(12) 0.8924(3) 0.0562(15) Uani 1 1 d . . . . .
H27A H 1.2033 0.8827 0.9480 0.084 Uiso 1 1 calc R U . . .
H27B H 1.1566 1.0815 0.9119 0.084 Uiso 1 1 calc R U . . .
H27C H 1.2154 0.9506 0.8437 0.084 Uiso 1 1 calc R 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
N1 C12 1.412(4) . ?
N1 B1 1.414(5) . ?
N1 C19 1.452(5) . ?
B1 C1 1.551(6) . ?
B1 C14 1.576(5) . ?
Br1 C11 1.896(4) . ?
Br2 C3 1.891(3) . ?
C1 C2 1.408(5) . ?
C1 C6 1.412(5) . ?
C2 C3 1.380(6) . ?
C3 C4 1.390(6) . ?
C4 C5 1.376(6) . ?
C5 C6 1.407(6) . ?
C6 C7 1.466(5) . ?
C7 C8 1.403(5) . ?
C7 C12 1.421(5) . ?
C8 C10 1.377(6) . ?
C9 C11 1.378(5) . ?
C9 C12 1.403(5) . ?
C10 C11 1.390(6) . ?
C13 C26 1.382(6) . ?
C13 C14 1.402(6) . ?
C14 C15 1.398(5) . ?
C15 C24 1.390(6) . ?
C16 C21 1.387(5) . ?
C16 C19 1.397(5) . ?
C16 C17 1.496(5) . ?
C18 C19 1.392(5) . ?
C18 C23 1.399(6) . ?
C18 C20 1.510(7) . ?
C21 C22 1.393(6) . ?
C22 C23 1.383(7) . ?
C22 C27 1.503(6) . ?
C24 C25 1.378(7) . ?
C25 C26 1.384(6) . ?

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
C12 N1 B1 123.2(3) . . ?
C12 N1 C19 116.1(3) . . ?
B1 N1 C19 120.7(3) . . ?
N1 B1 C1 116.0(3) . . ?
N1 B1 C14 121.8(3) . . ?
C1 B1 C14 122.2(3) . . ?
C2 C1 C6 118.8(3) . . ?
C2 C1 B1 121.2(3) . . ?
C6 C1 B1 119.9(3) . . ?
C3 C2 C1 120.4(4) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 Br2 119.5(3) . . ?
C4 C3 Br2 119.4(3) . . ?
C5 C4 C3 119.2(4) . . ?
C4 C5 C6 121.4(4) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 121.8(3) . . ?
C1 C6 C7 119.1(3) . . ?
C8 C7 C12 117.4(3) . . ?
C8 C7 C6 121.8(3) . . ?
C12 C7 C6 120.8(3) . . ?
C10 C8 C7 123.0(4) . . ?
C11 C9 C12 119.8(4) . . ?
C8 C10 C11 118.1(3) . . ?
C9 C11 C10 121.8(3) . . ?
C9 C11 Br1 119.7(3) . . ?
C10 C11 Br1 118.4(3) . . ?
C9 C12 N1 120.2(3) . . ?
C9 C12 C7 119.8(3) . . ?
N1 C12 C7 120.0(3) . . ?
C26 C13 C14 121.9(3) . . ?
C15 C14 C13 116.8(3) . . ?
C15 C14 B1 124.5(3) . . ?
C13 C14 B1 118.7(3) . . ?
C24 C15 C14 121.2(4) . . ?
C21 C16 C19 117.9(4) . . ?
C21 C16 C17 120.9(3) . . ?
C19 C16 C17 121.1(4) . . ?
C19 C18 C23 117.6(4) . . ?
C19 C18 C20 121.5(3) . . ?
C23 C18 C20 120.9(4) . . ?
C18 C19 C16 122.0(3) . . ?
C18 C19 N1 118.2(3) . . ?
C16 C19 N1 119.8(3) . . ?
C16 C21 C22 122.0(4) . . ?
C23 C22 C21 118.2(4) . . ?
C23 C22 C27 121.2(5) . . ?
C21 C22 C27 120.4(5) . . ?
C22 C23 C18 122.1(4) . . ?
C25 C24 C15 120.8(4) . . ?
C24 C25 C26 119.1(4) . . ?
C25 C26 C13 120.2(4) . . ?

_refine_diff_density_max         0.608
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.060



