# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1052259'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Br N3 O3'
_chemical_formula_weight         554.43

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) '
_chemical_absolute_configuration ad

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                   10.8543(2)
_cell_length_b                   13.1630(2)
_cell_length_c                   17.7406(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2534.69(7)
_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            white
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    1.660
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5864
_exptl_absorpt_correction_T_max  0.6447
_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  'CCD area detector'
_diffrn_measurement_method       'pi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13755
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4435
_reflns_number_gt                3776
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0280P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    'riding mode'
_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   0.012(7)
_refine_ls_number_reflns         4435
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0766
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.30462(3) 0.78359(2) 0.91165(2) 0.07022(13) Uani 1 1 d . . .
N3 N -0.12401(19) 1.16403(16) 0.87042(11) 0.0374(5) Uani 1 1 d . . .
O1 O 0.02022(17) 1.25614(13) 0.93669(10) 0.0461(5) Uani 1 1 d . . .
N1 N -0.1870(2) 1.23748(15) 1.04921(11) 0.0402(5) Uani 1 1 d . . .
H1A H -0.2552 1.2685 1.0404 0.048 Uiso 1 1 calc R . .
C17 C 0.1959(3) 0.88036(19) 0.95561(15) 0.0435(6) Uani 1 1 d . . .
C3 C -0.0502(2) 1.09608(18) 1.05714(13) 0.0328(5) Uani 1 1 d . . .
H3A H -0.1023 1.0569 1.0916 0.039 Uiso 1 1 calc R . .
N2 N 0.0569(2) 1.15075(19) 1.17600(13) 0.0466(6) Uani 1 1 d . . .
C6 C -0.2217(2) 1.09771(18) 0.88801(13) 0.0363(6) Uani 1 1 d . . .
C27 C -0.2972(3) 1.0452(2) 0.83965(15) 0.0467(6) Uani 1 1 d . . .
H27A H -0.2892 1.0519 0.7877 0.056 Uiso 1 1 calc R . .
C7 C -0.2344(2) 1.08991(19) 0.96529(14) 0.0354(6) Uani 1 1 d . . .
C14 C 0.0385(2) 1.02204(17) 1.02089(14) 0.0337(6) Uani 1 1 d . . .
C5 C -0.0686(2) 1.19913(18) 0.93427(13) 0.0356(6) Uani 1 1 d . . .
C1 C -0.1045(2) 1.26100(18) 1.11297(14) 0.0382(6) Uani 1 1 d . . .
H1B H -0.0718 1.3297 1.1058 0.046 Uiso 1 1 calc R . .
C28 C -0.3865(3) 0.9816(2) 0.87092(19) 0.0544(8) Uani 1 1 d . . .
H28A H -0.4389 0.9453 0.8394 0.065 Uiso 1 1 calc R . .
C22 C 0.0756(3) 1.0469(2) 0.79619(16) 0.0509(7) Uani 1 1 d . . .
H22A H 0.0879 1.0595 0.8472 0.061 Uiso 1 1 calc R . .
O3 O 0.1296(2) 1.2087(2) 1.20554(13) 0.0727(6) Uani 1 1 d . . .
C2 C 0.0035(2) 1.18358(18) 1.10205(14) 0.0364(5) Uani 1 1 d . . .
H2A H 0.0684 1.2160 1.0721 0.044 Uiso 1 1 calc R . .
C21 C -0.0127(2) 1.10134(19) 0.75714(14) 0.0375(6) Uani 1 1 d . . .
C10 C -0.3107(3) 1.1850(2) 1.27891(18) 0.0616(8) Uani 1 1 d . . .
H10A H -0.3731 1.1389 1.2898 0.074 Uiso 1 1 calc R . .
C4 C -0.1381(2) 1.15480(17) 1.00279(14) 0.0340(5) Uani 1 1 d . . .
C8 C -0.1661(2) 1.25635(18) 1.18994(14) 0.0392(6) Uani 1 1 d . . .
C30 C -0.3218(2) 1.0268(2) 0.99596(16) 0.0457(7) Uani 1 1 d . . .
H30A H -0.3299 1.0210 1.0480 0.055 Uiso 1 1 calc R . .
C20 C -0.0823(3) 1.1873(2) 0.79438(14) 0.0440(7) Uani 1 1 d . . .
H20A H -0.0295 1.2467 0.7962 0.053 Uiso 1 1 calc R . .
H20B H -0.1533 1.2041 0.7636 0.053 Uiso 1 1 calc R . .
C15 C 0.1606(2) 1.0456(2) 1.00576(15) 0.0402(6) Uani 1 1 d . . .
H15A H 0.1905 1.1098 1.0178 0.048 Uiso 1 1 calc R . .
C19 C -0.0023(3) 0.92541(19) 1.00196(17) 0.0489(7) Uani 1 1 d . . .
H19A H -0.0839 0.9082 1.0116 0.059 Uiso 1 1 calc R . .
C24 C 0.1275(3) 0.9524(2) 0.68578(18) 0.0531(8) Uani 1 1 d . . .
H24A H 0.1739 0.9024 0.6620 0.064 Uiso 1 1 calc R . .
C23 C 0.1462(3) 0.9737(2) 0.76012(18) 0.0583(8) Uani 1 1 d . . .
H23A H 0.2067 0.9389 0.7868 0.070 Uiso 1 1 calc R . .
C29 C -0.3979(3) 0.9717(2) 0.94788(18) 0.0544(8) Uani 1 1 d . . .
H29A H -0.4568 0.9279 0.9678 0.065 Uiso 1 1 calc R . .
C26 C -0.0302(3) 1.0788(2) 0.68157(16) 0.0520(7) Uani 1 1 d . . .
H26A H -0.0899 1.1135 0.6542 0.062 Uiso 1 1 calc R . .
C9 C -0.2585(3) 1.1884(2) 1.20733(16) 0.0471(7) Uani 1 1 d . . .
H9A H -0.2865 1.1439 1.1704 0.057 Uiso 1 1 calc R . .
C16 C 0.2388(3) 0.9750(2) 0.97308(16) 0.0471(7) Uani 1 1 d . . .
H16A H 0.3204 0.9920 0.9631 0.056 Uiso 1 1 calc R . .
O2 O 0.0233(2) 1.07074(18) 1.20315(12) 0.0652(6) Uani 1 1 d . . .
C12 C -0.1785(4) 1.3204(3) 1.31677(19) 0.0729(10) Uani 1 1 d . . .
H12A H -0.1513 1.3656 1.3535 0.088 Uiso 1 1 calc R . .
C13 C -0.1274(3) 1.3232(2) 1.24468(17) 0.0570(8) Uani 1 1 d . . .
H13A H -0.0667 1.3707 1.2335 0.068 Uiso 1 1 calc R . .
C18 C 0.0741(3) 0.8540(2) 0.96936(18) 0.0552(8) Uani 1 1 d . . .
H18A H 0.0447 0.7898 0.9569 0.066 Uiso 1 1 calc R . .
C11 C -0.2683(4) 1.2514(3) 1.33361(19) 0.0726(11) Uani 1 1 d . . .
H11A H -0.3011 1.2490 1.3820 0.087 Uiso 1 1 calc R . .
C25 C 0.0403(3) 1.0051(3) 0.64652(18) 0.0599(9) Uani 1 1 d . . .
H25B H 0.0282 0.9913 0.5956 0.072 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 C17 1.903(3) . ?
N3 C5 1.363(3) . ?
N3 C6 1.408(3) . ?
N3 C20 1.455(3) . ?
O1 C5 1.222(3) . ?
N1 C4 1.464(3) . ?
N1 C1 1.475(3) . ?
C17 C16 1.365(4) . ?
C17 C18 1.389(4) . ?
C3 C14 1.513(3) . ?
C3 C2 1.517(3) . ?
C3 C4 1.561(3) . ?
N2 O2 1.214(3) . ?
N2 O3 1.216(3) . ?
N2 C2 1.498(3) . ?
C6 C27 1.373(4) . ?
C6 C7 1.382(3) . ?
C27 C28 1.396(4) . ?
C7 C30 1.374(3) . ?
C7 C4 1.505(3) . ?
C14 C15 1.388(3) . ?
C14 C19 1.388(4) . ?
C5 C4 1.545(3) . ?
C1 C8 1.521(4) . ?
C1 C2 1.566(3) . ?
C28 C29 1.377(4) . ?
C22 C21 1.383(4) . ?
C22 C23 1.388(4) . ?
C21 C26 1.386(4) . ?
C21 C20 1.512(4) . ?
C10 C11 1.385(5) . ?
C10 C9 1.391(4) . ?
C8 C13 1.376(4) . ?
C8 C9 1.378(4) . ?
C30 C29 1.392(4) . ?
C15 C16 1.386(4) . ?
C19 C18 1.380(4) . ?
C24 C23 1.363(4) . ?
C24 C25 1.364(4) . ?
C26 C25 1.384(4) . ?
C12 C11 1.365(5) . ?
C12 C13 1.395(5) . ?

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
C5 N3 C6 110.99(19) . . ?
C5 N3 C20 124.2(2) . . ?
C6 N3 C20 124.7(2) . . ?
C4 N1 C1 111.55(18) . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 Br1 119.5(2) . . ?
C18 C17 Br1 119.7(2) . . ?
C14 C3 C2 117.9(2) . . ?
C14 C3 C4 116.4(2) . . ?
C2 C3 C4 100.56(18) . . ?
O2 N2 O3 124.6(3) . . ?
O2 N2 C2 118.8(2) . . ?
O3 N2 C2 116.6(2) . . ?
C27 C6 C7 121.5(2) . . ?
C27 C6 N3 128.5(2) . . ?
C7 C6 N3 109.9(2) . . ?
C6 C27 C28 117.9(3) . . ?
C30 C7 C6 120.5(2) . . ?
C30 C7 C4 130.4(2) . . ?
C6 C7 C4 109.1(2) . . ?
C15 C14 C19 117.5(2) . . ?
C15 C14 C3 123.1(2) . . ?
C19 C14 C3 119.4(2) . . ?
O1 C5 N3 125.8(2) . . ?
O1 C5 C4 126.1(2) . . ?
N3 C5 C4 108.1(2) . . ?
N1 C1 C8 114.4(2) . . ?
N1 C1 C2 102.88(18) . . ?
C8 C1 C2 114.45(19) . . ?
C29 C28 C27 120.9(3) . . ?
C21 C22 C23 120.8(3) . . ?
N2 C2 C3 112.9(2) . . ?
N2 C2 C1 111.66(19) . . ?
C3 C2 C1 105.75(19) . . ?
C22 C21 C26 118.0(3) . . ?
C22 C21 C20 121.0(2) . . ?
C26 C21 C20 120.9(2) . . ?
C11 C10 C9 118.9(3) . . ?
N1 C4 C7 114.74(19) . . ?
N1 C4 C5 109.80(19) . . ?
C7 C4 C5 101.9(2) . . ?
N1 C4 C3 104.01(19) . . ?
C7 C4 C3 114.61(19) . . ?
C5 C4 C3 112.00(18) . . ?
C13 C8 C9 118.6(3) . . ?
C13 C8 C1 118.3(3) . . ?
C9 C8 C1 123.1(2) . . ?
C7 C30 C29 118.9(3) . . ?
N3 C20 C21 113.8(2) . . ?
C16 C15 C14 121.1(2) . . ?
C18 C19 C14 122.3(3) . . ?
C23 C24 C25 119.5(3) . . ?
C24 C23 C22 120.4(3) . . ?
C28 C29 C30 120.3(3) . . ?
C25 C26 C21 120.6(3) . . ?
C8 C9 C10 121.4(3) . . ?
C17 C16 C15 119.9(3) . . ?
C11 C12 C13 120.2(3) . . ?
C8 C13 C12 120.6(3) . . ?
C19 C18 C17 118.4(3) . . ?
C12 C11 C10 120.2(3) . . ?
C24 C25 C26 120.7(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.037
