# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1563576'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2017-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ?
;
_chemical_absolute_configuration ad
_chemical_name_common            KMK
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 Br N2 O2'
_chemical_formula_weight         410.28

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   20.508(7)
_cell_length_b                   7.052(2)
_cell_length_c                   15.829(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.795(15)
_cell_angle_gamma                90.00
_cell_volume                     1966.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1629
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      19.42

_exptl_crystal_description       cubic
_exptl_crystal_colour            lucid
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    2.107
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5706
_exptl_absorpt_correction_T_max  0.7861
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7764
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_sigmaI/netI    0.1317
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3641
_reflns_number_gt                1706
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.061(14)
_refine_ls_number_reflns         3641
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.31322(3) -0.07406(19) 0.82498(5) 0.0941(3) Uani 1 1 d . . .
O1 O 0.5623(3) 0.6764(8) 0.9082(4) 0.0822(17) Uani 1 1 d . . .
O2 O 0.6051(4) 0.2711(8) 0.7491(4) 0.111(3) Uani 1 1 d . . .
N1 N 0.6288(3) 0.5808(9) 0.7851(4) 0.0604(16) Uani 1 1 d . . .
H1A H 0.6393 0.6606 0.8315 0.072 Uiso 1 1 calc R . .
C15 C 0.5095(3) 0.1937(9) 0.8829(4) 0.0505(17) Uani 1 1 d . . .
C19 C 0.5890(4) 0.1675(10) 0.9043(5) 0.064(2) Uani 1 1 d . . .
H19 H 0.6162 0.0550 0.9172 0.077 Uiso 1 1 calc R . .
C18 C 0.6155(3) 0.3725(7) 0.9000(4) 0.0513(19) Uani 1 1 d . . .
C17 C 0.5545(4) 0.5093(10) 0.8971(4) 0.0630(19) Uani 1 1 d . . .
C16 C 0.4909(3) 0.3875(10) 0.8769(4) 0.0509(18) Uani 1 1 d . . .
C8 C 0.6270(3) 0.6543(9) 0.6996(4) 0.0585(16) Uani 1 1 d . . .
C12 C 0.3653(3) 0.3021(9) 0.8362(4) 0.0641(18) Uani 1 1 d . . .
H12A H 0.3161 0.3356 0.8184 0.077 Uiso 1 1 calc R . .
C14 C 0.4576(3) 0.0565(8) 0.8685(4) 0.0522(15) Uani 1 1 d . . .
H14A H 0.4703 -0.0714 0.8746 0.063 Uiso 1 1 calc R . .
C13 C 0.3865(3) 0.1129(10) 0.8449(4) 0.0611(17) Uani 1 1 d . . .
C21 C 0.6910(3) 0.4177(15) 0.9833(4) 0.0654(16) Uani 1 1 d . . .
C5 C 0.6214(3) 0.8189(9) 0.5360(4) 0.0613(17) Uani 1 1 d . . .
C11 C 0.4176(3) 0.4361(15) 0.8539(4) 0.0702(16) Uani 1 1 d . . .
H11A H 0.4047 0.5633 0.8507 0.084 Uiso 1 1 calc R . .
C20 C 0.6159(3) 0.4005(13) 0.8012(4) 0.0564(16) Uani 1 1 d . . .
C9 C 0.6431(3) 0.8406(9) 0.7001(4) 0.0648(18) Uani 1 1 d . . .
H9A H 0.6558 0.9143 0.7551 0.078 Uiso 1 1 calc R . .
N2 N 0.7491(3) 0.4544(14) 1.0475(4) 0.094(2) Uani 1 1 d . . .
C6 C 0.6060(4) 0.6273(10) 0.5378(4) 0.086(2) Uani 1 1 d . . .
H6A H 0.5942 0.5529 0.4832 0.103 Uiso 1 1 calc R . .
C4 C 0.6189(3) 0.9152(17) 0.4458(4) 0.0771(18) Uani 1 1 d . . .
C10 C 0.6408(3) 0.9214(14) 0.6194(4) 0.0715(15) Uani 1 1 d . . .
H10A H 0.6527 1.0492 0.6215 0.086 Uiso 1 1 calc R . .
C7 C 0.6076(4) 0.5448(8) 0.6167(5) 0.082(2) Uani 1 1 d . . .
H7A H 0.5958 0.4170 0.6152 0.099 Uiso 1 1 calc R . .
C3 C 0.6969(4) 0.9689(16) 0.4724(5) 0.134(4) Uani 1 1 d . . .
H3A H 0.7282 0.8575 0.4909 0.201 Uiso 1 1 calc R . .
H3B H 0.7175 1.0562 0.5266 0.201 Uiso 1 1 calc R . .
H3C H 0.6958 1.0279 0.4170 0.201 Uiso 1 1 calc R . .
C1 C 0.5911(6) 0.7724(13) 0.3614(6) 0.162(5) Uani 1 1 d . . .
H1B H 0.6245 0.6649 0.3826 0.243 Uiso 1 1 calc R . .
H1C H 0.5906 0.8312 0.3063 0.243 Uiso 1 1 calc R . .
H1D H 0.5407 0.7315 0.3422 0.243 Uiso 1 1 calc R . .
C2 C 0.5700(6) 1.0802(15) 0.4169(7) 0.187(5) Uani 1 1 d . . .
H2A H 0.5198 1.0420 0.4001 0.281 Uiso 1 1 calc R . .
H2B H 0.5681 1.1392 0.3611 0.281 Uiso 1 1 calc R . .
H2C H 0.5897 1.1687 0.4706 0.281 Uiso 1 1 calc R . .


_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
Br1 C13 1.901(6) . ?
O1 C17 1.190(7) . ?
O2 C20 1.172(8) . ?
N1 C20 1.349(9) . ?
N1 C8 1.432(7) . ?
N1 H1A 0.8600 . ?
C15 C14 1.369(7) . ?
C15 C16 1.410(9) . ?
C15 C19 1.496(8) . ?
C19 C18 1.559(8) . ?
C19 H19 0.9300 . ?
C18 C21 1.465(7) . ?
C18 C17 1.562(7) . ?
C18 C20 1.580(7) . ?
C17 C16 1.455(8) . ?
C16 C11 1.394(7) . ?
C8 C9 1.354(7) . ?
C8 C7 1.394(7) . ?
C12 C11 1.347(10) . ?
C12 C13 1.388(8) . ?
C12 H12A 0.9300 . ?
C14 C13 1.365(7) . ?
C14 H14A 0.9300 . ?
C21 N2 1.131(6) . ?
C5 C10 1.374(8) . ?
C5 C6 1.391(8) . ?
C5 C4 1.558(8) . ?
C11 H11A 0.9300 . ?
C9 C10 1.376(7) . ?
C9 H9A 0.9300 . ?
C6 C7 1.363(7) . ?
C6 H6A 0.9300 . ?
C4 C2 1.449(12) . ?
C4 C3 1.481(8) . ?
C4 C1 1.532(11) . ?
C10 H10A 0.9300 . ?
C7 H7A 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C20 N1 C8 127.4(5) . . ?
C20 N1 H1A 116.3 . . ?
C8 N1 H1A 116.3 . . ?
C14 C15 C16 120.9(5) . . ?
C14 C15 C19 127.9(6) . . ?
C16 C15 C19 111.2(6) . . ?
C15 C19 C18 103.9(5) . . ?
C15 C19 H19 128.1 . . ?
C18 C19 H19 128.1 . . ?
C21 C18 C19 113.2(6) . . ?
C21 C18 C17 110.7(5) . . ?
C19 C18 C17 106.4(5) . . ?
C21 C18 C20 108.9(4) . . ?
C19 C18 C20 109.8(5) . . ?
C17 C18 C20 107.7(5) . . ?
O1 C17 C16 130.9(7) . . ?
O1 C17 C18 124.2(7) . . ?
C16 C17 C18 104.9(5) . . ?
C11 C16 C15 118.4(7) . . ?
C11 C16 C17 129.6(7) . . ?
C15 C16 C17 112.1(6) . . ?
C9 C8 C7 119.6(6) . . ?
C9 C8 N1 117.3(6) . . ?
C7 C8 N1 123.1(6) . . ?
C11 C12 C13 118.6(6) . . ?
C11 C12 H12A 120.7 . . ?
C13 C12 H12A 120.7 . . ?
C13 C14 C15 118.0(6) . . ?
C13 C14 H14A 121.0 . . ?
C15 C14 H14A 121.0 . . ?
C14 C13 C12 122.9(6) . . ?
C14 C13 Br1 119.1(5) . . ?
C12 C13 Br1 118.0(5) . . ?
N2 C21 C18 179.3(12) . . ?
C10 C5 C6 116.6(6) . . ?
C10 C5 C4 120.6(7) . . ?
C6 C5 C4 122.8(7) . . ?
C12 C11 C16 121.2(8) . . ?
C12 C11 H11A 119.4 . . ?
C16 C11 H11A 119.4 . . ?
O2 C20 N1 125.8(5) . . ?
O2 C20 C18 120.2(7) . . ?
N1 C20 C18 113.9(6) . . ?
C8 C9 C10 120.3(7) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C7 C6 C5 122.3(6) . . ?
C7 C6 H6A 118.9 . . ?
C5 C6 H6A 118.9 . . ?
C2 C4 C3 111.0(10) . . ?
C2 C4 C1 111.4(6) . . ?
C3 C4 C1 106.4(7) . . ?
C2 C4 C5 109.4(6) . . ?
C3 C4 C5 109.1(5) . . ?
C1 C4 C5 109.6(8) . . ?
C9 C10 C5 122.0(8) . . ?
C9 C10 H10A 119.0 . . ?
C5 C10 H10A 119.0 . . ?
C6 C7 C8 119.2(6) . . ?
C6 C7 H7A 120.4 . . ?
C8 C7 H7A 120.4 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.066
