# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_131231wl_0m
_database_code_depnum_ccdc_archive 'CCDC 1416442'
_audit_update_record             
;
2015-08-02 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration 8R
_chemical_formula_sum            'C19 H19 Br N2 O2'
_chemical_formula_weight         387.27

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                   5.5598(9)
_cell_length_b                   16.478(3)
_cell_length_c                   19.769(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1811.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    2.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5574
_exptl_absorpt_correction_T_max  0.5777
_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  ?
_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            11942
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         26.49
_reflns_number_total             3733
_reflns_number_gt                2349
_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)+(0.0213P)²+0.5012P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(13)
_refine_ls_number_reflns         3733
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.89933(15) 0.39400(3) 1.06196(3) 0.1240(3) Uani 1 1 d . . .
C1 C 0.7764(9) 0.3640(2) 0.97627(18) 0.0704(12) Uani 1 1 d . . .
C2 C 0.8809(8) 0.3003(2) 0.94231(18) 0.0683(10) Uani 1 1 d . . .
H2 H 1.0132 0.2735 0.9605 0.082 Uiso 1 1 calc R . .
C3 C 0.7872(7) 0.2768(2) 0.88132(17) 0.0566(10) Uani 1 1 d . . .
H3 H 0.8589 0.2342 0.8580 0.068 Uiso 1 1 calc R . .
C4 C 0.5880(6) 0.31505(17) 0.85349(15) 0.0456(8) Uani 1 1 d . . .
C5 C 0.4881(7) 0.3792(2) 0.88963(18) 0.0608(10) Uani 1 1 d . . .
H5 H 0.3550 0.4062 0.8722 0.073 Uiso 1 1 calc R . .
C6 C 0.5824(9) 0.4034(2) 0.95079(18) 0.0726(11) Uani 1 1 d . . .
H6 H 0.5137 0.4463 0.9744 0.087 Uiso 1 1 calc R . .
C7 C 0.4908(6) 0.2892(2) 0.78735(16) 0.0482(8) Uani 1 1 d . . .
C8 C 0.3548(8) 0.2503(2) 0.65614(19) 0.0664(11) Uani 1 1 d . . .
H8 H 0.2823 0.2158 0.6213 0.080 Uiso 1 1 calc R . .
C9 C 0.1634(7) 0.2816(3) 0.7029(2) 0.0732(11) Uani 1 1 d . . .
H9A H 0.0756 0.2363 0.7223 0.088 Uiso 1 1 calc R . .
H9B H 0.0506 0.3148 0.6777 0.088 Uiso 1 1 calc R . .
C10 C 0.2762(7) 0.3313(2) 0.75868(18) 0.0598(9) Uani 1 1 d . . .
H10A H 0.3239 0.3838 0.7409 0.072 Uiso 1 1 calc R . .
H10B H 0.1589 0.3403 0.7942 0.072 Uiso 1 1 calc R . .
C11 C 0.5901(13) 0.3046(3) 0.5662(2) 0.1171(19) Uani 1 1 d . . .
H11A H 0.4894 0.2728 0.5361 0.141 Uiso 1 1 calc R . .
H11B H 0.7324 0.2726 0.5760 0.141 Uiso 1 1 calc R . .
C12 C 0.660(2) 0.3747(3) 0.5327(3) 0.196(5) Uani 1 1 d . . .
H12A H 0.5199 0.4031 0.5170 0.293 Uiso 1 1 calc R . .
H12B H 0.7597 0.3607 0.4949 0.293 Uiso 1 1 calc R . .
H12C H 0.7485 0.4088 0.5632 0.293 Uiso 1 1 calc R . .
C13 C 0.6311(7) 0.1343(2) 0.66958(17) 0.0559(9) Uani 1 1 d . . .
C14 C 0.7965(6) 0.08645(19) 0.71334(17) 0.0524(9) Uani 1 1 d . . .
C15 C 0.7550(7) 0.0685(2) 0.78055(18) 0.0586(9) Uani 1 1 d . . .
H15 H 0.6187 0.0885 0.8021 0.070 Uiso 1 1 calc R . .
C16 C 0.9167(8) 0.0205(2) 0.81591(19) 0.0701(11) Uani 1 1 d . . .
H16 H 0.8870 0.0081 0.8610 0.084 Uiso 1 1 calc R . .
C17 C 1.1188(8) -0.0087(2) 0.7853(3) 0.0764(12) Uani 1 1 d . . .
H17 H 1.2287 -0.0394 0.8098 0.092 Uiso 1 1 calc R . .
C18 C 1.1590(8) 0.0071(3) 0.7190(3) 0.0758(12) Uani 1 1 d . . .
H18 H 1.2960 -0.0133 0.6980 0.091 Uiso 1 1 calc R . .
C19 C 0.9993(7) 0.0530(2) 0.6827(2) 0.0644(10) Uani 1 1 d . . .
H19 H 1.0265 0.0620 0.6369 0.077 Uiso 1 1 calc R . .
N1 N 0.6018(6) 0.22968(16) 0.75852(13) 0.0512(7) Uani 1 1 d . . .
N2 N 0.5253(5) 0.20342(17) 0.69590(13) 0.0530(7) Uani 1 1 d . . .
O1 O 0.4659(6) 0.31759(16) 0.62596(13) 0.0838(9) Uani 1 1 d . . .
O2 O 0.5886(6) 0.11344(16) 0.61212(13) 0.0790(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
Br1 C1 1.892(4) . ?
C1 C6 1.356(6) . ?
C1 C2 1.375(5) . ?
C2 C3 1.369(5) . ?
C3 C4 1.388(5) . ?
C4 C5 1.391(4) . ?
C4 C7 1.477(5) . ?
C5 C6 1.377(5) . ?
C7 N1 1.291(4) . ?
C7 C10 1.493(5) . ?
C8 O1 1.403(5) . ?
C8 N2 1.454(5) . ?
C8 C9 1.501(6) . ?
C9 C10 1.511(5) . ?
C11 O1 1.386(5) . ?
C11 C12 1.386(7) . ?
C13 O2 1.210(4) . ?
C13 N2 1.383(4) . ?
C13 C14 1.489(5) . ?
C14 C15 1.381(5) . ?
C14 C19 1.393(5) . ?
C15 C16 1.386(5) . ?
C16 C17 1.364(6) . ?
C17 C18 1.355(6) . ?
C18 C19 1.370(6) . ?
N1 N2 1.379(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 121.3(4) . . ?
C6 C1 Br1 119.7(3) . . ?
C2 C1 Br1 118.9(3) . . ?
C3 C2 C1 119.0(4) . . ?
C2 C3 C4 121.6(3) . . ?
C3 C4 C5 117.4(3) . . ?
C3 C4 C7 120.8(3) . . ?
C5 C4 C7 121.8(3) . . ?
C6 C5 C4 121.3(4) . . ?
C1 C6 C5 119.4(4) . . ?
N1 C7 C4 115.8(3) . . ?
N1 C7 C10 124.6(3) . . ?
C4 C7 C10 119.6(3) . . ?
O1 C8 N2 111.3(3) . . ?
O1 C8 C9 107.6(3) . . ?
N2 C8 C9 108.2(3) . . ?
C8 C9 C10 110.0(3) . . ?
C7 C10 C9 110.9(3) . . ?
O1 C11 C12 114.6(5) . . ?
O2 C13 N2 120.2(3) . . ?
O2 C13 C14 121.1(3) . . ?
N2 C13 C14 118.7(3) . . ?
C15 C14 C19 118.0(4) . . ?
C15 C14 C13 124.7(3) . . ?
C19 C14 C13 117.1(3) . . ?
C14 C15 C16 120.0(4) . . ?
C17 C16 C15 120.8(4) . . ?
C18 C17 C16 119.8(4) . . ?
C17 C18 C19 120.4(4) . . ?
C18 C19 C14 121.0(4) . . ?
C7 N1 N2 119.2(3) . . ?
N1 N2 C13 117.7(3) . . ?
N1 N2 C8 121.3(3) . . ?
C13 N2 C8 120.8(3) . . ?
C11 O1 C8 117.4(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
C6 C1 C2 C3 0.5(6) . . . . ?
Br1 C1 C2 C3 177.9(3) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C2 C3 C4 C7 179.5(3) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C7 C4 C5 C6 -179.1(3) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
Br1 C1 C6 C5 -177.5(3) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C3 C4 C7 N1 0.4(4) . . . . ?
C5 C4 C7 N1 179.1(3) . . . . ?
C3 C4 C7 C10 179.9(3) . . . . ?
C5 C4 C7 C10 -1.4(5) . . . . ?
O1 C8 C9 C10 -63.1(4) . . . . ?
N2 C8 C9 C10 57.2(4) . . . . ?
N1 C7 C10 C9 16.1(5) . . . . ?
C4 C7 C10 C9 -163.4(3) . . . . ?
C8 C9 C10 C7 -45.5(5) . . . . ?
O2 C13 C14 C15 -137.1(4) . . . . ?
N2 C13 C14 C15 42.7(5) . . . . ?
O2 C13 C14 C19 38.4(5) . . . . ?
N2 C13 C14 C19 -141.9(3) . . . . ?
C19 C14 C15 C16 1.9(5) . . . . ?
C13 C14 C15 C16 177.3(3) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C15 C16 C17 C18 -2.0(6) . . . . ?
C16 C17 C18 C19 0.7(6) . . . . ?
C17 C18 C19 C14 2.0(6) . . . . ?
C15 C14 C19 C18 -3.3(5) . . . . ?
C13 C14 C19 C18 -179.0(3) . . . . ?
C4 C7 N1 N2 -178.4(3) . . . . ?
C10 C7 N1 N2 2.1(5) . . . . ?
C7 N1 N2 C13 -173.4(3) . . . . ?
C7 N1 N2 C8 11.8(5) . . . . ?
O2 C13 N2 N1 -172.4(3) . . . . ?
C14 C13 N2 N1 7.8(5) . . . . ?
O2 C13 N2 C8 2.4(5) . . . . ?
C14 C13 N2 C8 -177.4(3) . . . . ?
O1 C8 N2 N1 76.1(4) . . . . ?
C9 C8 N2 N1 -41.8(4) . . . . ?
O1 C8 N2 C13 -98.5(4) . . . . ?
C9 C8 N2 C13 143.5(3) . . . . ?
C12 C11 O1 C8 169.3(7) . . . . ?
N2 C8 O1 C11 82.2(5) . . . . ?
C9 C8 O1 C11 -159.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.039
