# Electronic Supplementary Material (ESI) for ChemComm.
# 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_160614lk_0m
_database_code_depnum_ccdc_archive 'CCDC 1813247'
_audit_update_record             
;
2017-12-23 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration 9S,10S
_chemical_formula_sum            'C23 H21 Br N2 O'
_chemical_formula_weight         421.33

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   5.9550(14)
_cell_length_b                   18.080(4)
_cell_length_c                   18.630(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2005.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    51
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    2.064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5957
_exptl_absorpt_correction_T_max  0.6160
_exptl_absorpt_process_details   SADABS

_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            13269
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         26.50
_reflns_number_total             4156
_reflns_number_gt                2414
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0135P)²+0.2733P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(11)
_refine_ls_number_reflns         4156
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.19998(11) 0.28411(3) -0.15584(2) 0.1034(3) Uani 1 1 d . . .
C1 C -0.0844(8) 0.32980(19) -0.07192(19) 0.0597(11) Uani 1 1 d . . .
C2 C -0.1948(8) 0.31943(18) -0.00789(19) 0.0596(10) Uani 1 1 d . . .
H2 H -0.3242 0.2907 -0.0059 0.072 Uiso 1 1 calc R . .
C3 C -0.1103(7) 0.35249(19) 0.05358(19) 0.0550(10) Uani 1 1 d . . .
H3 H -0.1829 0.3454 0.0972 0.066 Uiso 1 1 calc R . .
C4 C 0.0820(6) 0.39612(17) 0.05060(18) 0.0488(9) Uani 1 1 d . . .
C5 C 0.1906(7) 0.40375(18) -0.01498(18) 0.0570(9) Uani 1 1 d . . .
H5 H 0.3217 0.4316 -0.0176 0.068 Uiso 1 1 calc R . .
C6 C 0.1085(8) 0.3711(2) -0.07583(19) 0.0638(11) Uani 1 1 d . . .
H6 H 0.1827 0.3769 -0.1194 0.077 Uiso 1 1 calc R . .
C7 C 0.1629(7) 0.43383(17) 0.11641(19) 0.0502(9) Uani 1 1 d . . .
C8 C 0.4076(7) 0.4517(2) 0.1272(2) 0.0626(11) Uani 1 1 d . . .
H8A H 0.4870 0.4460 0.0821 0.075 Uiso 1 1 calc R . .
H8B H 0.4720 0.4175 0.1616 0.075 Uiso 1 1 calc R . .
C9 C 0.4368(7) 0.53079(19) 0.1544(2) 0.0598(10) Uani 1 1 d . . .
H9 H 0.5874 0.5363 0.1750 0.072 Uiso 1 1 calc R . .
C10 C 0.2607(7) 0.5475(2) 0.21250(19) 0.0659(11) Uani 1 1 d . . .
H10 H 0.3358 0.5611 0.2574 0.079 Uiso 1 1 calc R . .
C11 C 0.1345(9) 0.6119(2) 0.1840(3) 0.0855(15) Uani 1 1 d . . .
H11 H 0.0160 0.6345 0.2080 0.103 Uiso 1 1 calc R . .
C12 C 0.2093(10) 0.6333(2) 0.1210(3) 0.0807(14) Uani 1 1 d . . .
H12 H 0.1465 0.6716 0.0943 0.097 Uiso 1 1 calc R . .
C13 C 0.3999(8) 0.5906(2) 0.0981(2) 0.0603(11) Uani 1 1 d . . .
C14 C 0.5301(8) 0.6019(2) 0.0406(2) 0.0706(12) Uani 1 1 d . . .
C15 C 0.7334(8) 0.5555(3) 0.0229(2) 0.0911(14) Uani 1 1 d . . .
H15A H 0.7760 0.5271 0.0643 0.137 Uiso 1 1 calc R . .
H15B H 0.8554 0.5871 0.0091 0.137 Uiso 1 1 calc R . .
H15C H 0.6981 0.5226 -0.0159 0.137 Uiso 1 1 calc R . .
C16 C 0.4910(10) 0.6646(2) -0.0121(3) 0.1034(17) Uani 1 1 d . . .
H16A H 0.3412 0.6833 -0.0064 0.155 Uiso 1 1 calc R . .
H16B H 0.5101 0.6466 -0.0602 0.155 Uiso 1 1 calc R . .
H16C H 0.5970 0.7035 -0.0031 0.155 Uiso 1 1 calc R . .
C17 C -0.0175(8) 0.4840(2) 0.2869(2) 0.0623(11) Uani 1 1 d . . .
C18 C -0.1916(8) 0.4260(2) 0.29713(17) 0.0586(10) Uani 1 1 d . . .
C19 C -0.1656(8) 0.3532(2) 0.2745(2) 0.0675(12) Uani 1 1 d . . .
H19 H -0.0387 0.3388 0.2489 0.081 Uiso 1 1 calc R . .
C20 C -0.3326(11) 0.3025(2) 0.2907(3) 0.0893(15) Uani 1 1 d . . .
H20 H -0.3171 0.2535 0.2765 0.107 Uiso 1 1 calc R . .
C21 C -0.5223(10) 0.3243(4) 0.3280(3) 0.1043(18) Uani 1 1 d . . .
H21 H -0.6352 0.2901 0.3375 0.125 Uiso 1 1 calc R . .
C22 C -0.5448(9) 0.3956(3) 0.3509(3) 0.0959(15) Uani 1 1 d . . .
H22 H -0.6716 0.4101 0.3763 0.115 Uiso 1 1 calc R . .
C23 C -0.3786(8) 0.4452(2) 0.3358(2) 0.0712(11) Uani 1 1 d . . .
H23 H -0.3926 0.4935 0.3523 0.085 Uiso 1 1 calc R . .
N1 N 0.0170(5) 0.44772(14) 0.16504(16) 0.0521(7) Uani 1 1 d . . .
N2 N 0.1069(5) 0.48402(16) 0.22522(16) 0.0581(9) Uani 1 1 d . . .
O1 O 0.0218(5) 0.52887(15) 0.33478(15) 0.0851(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
Br1 C1 1.898(4) . ?
C1 C6 1.372(6) . ?
C1 C2 1.375(5) . ?
C2 C3 1.386(5) . ?
C3 C4 1.392(5) . ?
C4 C5 1.389(5) . ?
C4 C7 1.483(5) . ?
C5 C6 1.368(5) . ?
C7 N1 1.280(4) . ?
C7 C8 1.506(5) . ?
C8 C9 1.526(5) . ?
C9 C13 1.522(5) . ?
C9 C10 1.537(5) . ?
C10 C11 1.484(6) . ?
C10 N2 1.487(5) . ?
C11 C12 1.315(6) . ?
C12 C13 1.438(6) . ?
C13 C14 1.338(6) . ?
C14 C15 1.510(6) . ?
C14 C16 1.518(6) . ?
C17 O1 1.228(4) . ?
C17 N2 1.368(5) . ?
C17 C18 1.486(6) . ?
C18 C23 1.371(6) . ?
C18 C19 1.391(5) . ?
C19 C20 1.386(6) . ?
C20 C21 1.383(7) . ?
C21 C22 1.363(7) . ?
C22 C23 1.365(6) . ?
N1 N2 1.405(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
C6 C1 C2 121.4(4) . . ?
C6 C1 Br1 119.8(3) . . ?
C2 C1 Br1 118.8(3) . . ?
C1 C2 C3 119.0(4) . . ?
C2 C3 C4 120.7(3) . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 C7 122.0(3) . . ?
C3 C4 C7 119.6(3) . . ?
C6 C5 C4 121.3(4) . . ?
C5 C6 C1 119.3(4) . . ?
N1 C7 C4 117.1(3) . . ?
N1 C7 C8 121.3(3) . . ?
C4 C7 C8 121.5(3) . . ?
C7 C8 C9 110.9(3) . . ?
C13 C9 C8 114.8(3) . . ?
C13 C9 C10 104.3(3) . . ?
C8 C9 C10 109.9(3) . . ?
C11 C10 N2 110.5(4) . . ?
C11 C10 C9 104.4(3) . . ?
N2 C10 C9 112.4(3) . . ?
C12 C11 C10 112.3(4) . . ?
C11 C12 C13 111.9(4) . . ?
C14 C13 C12 127.7(4) . . ?
C14 C13 C9 125.3(4) . . ?
C12 C13 C9 107.0(3) . . ?
C13 C14 C15 123.6(4) . . ?
C13 C14 C16 123.0(5) . . ?
C15 C14 C16 113.4(4) . . ?
O1 C17 N2 120.4(4) . . ?
O1 C17 C18 120.4(4) . . ?
N2 C17 C18 119.1(4) . . ?
C23 C18 C19 119.3(4) . . ?
C23 C18 C17 117.1(4) . . ?
C19 C18 C17 123.4(4) . . ?
C20 C19 C18 118.6(5) . . ?
C21 C20 C19 120.5(4) . . ?
C22 C21 C20 120.4(5) . . ?
C21 C22 C23 119.0(5) . . ?
C22 C23 C18 122.0(5) . . ?
C7 N1 N2 113.5(3) . . ?
C17 N2 N1 117.6(3) . . ?
C17 N2 C10 117.9(3) . . ?
N1 N2 C10 117.9(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.041
