# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ch18209
_database_code_depnum_ccdc_archive 'CCDC 1501651'
_audit_update_record             
;
2017-01-17 deposited with the CCDC.
2017-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 Br N3'
_chemical_formula_sum            'C26 H20 Br N3'
_chemical_formula_weight         454.36

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.542(5)
_cell_length_b                   11.051(6)
_cell_length_c                   11.500(7)
_cell_angle_alpha                105.75(2)
_cell_angle_beta                 108.68(2)
_cell_angle_gamma                95.23(2)
_cell_volume                     1084.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    982
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      17.49

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    1.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_T_max  0.9811
_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 APEX2'
_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            9487
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_sigmaI/netI    0.2121
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.09
_reflns_number_total             3787
_reflns_number_gt                1386
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0884P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2308
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.2086
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_refine_ls_shift/su_max          0.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8089(9) 0.3898(7) 0.2915(8) 0.058(2) Uani 1 1 d . . .
C2 C 0.6937(10) 0.4511(7) 0.2695(7) 0.060(2) Uani 1 1 d . . .
H2 H 0.6140 0.4311 0.2952 0.072 Uiso 1 1 calc R . .
C3 C 0.6910(8) 0.5435(6) 0.2093(7) 0.048(2) Uani 1 1 d . . .
H3 H 0.6095 0.5849 0.1950 0.057 Uiso 1 1 calc R . .
C4 C 0.8087(8) 0.5758(6) 0.1695(7) 0.0416(19) Uani 1 1 d . . .
C5 C 0.9259(8) 0.5092(7) 0.1941(8) 0.064(2) Uani 1 1 d . . .
H5 H 1.0074 0.5282 0.1701 0.077 Uiso 1 1 calc R . .
C6 C 0.9253(9) 0.4167(8) 0.2525(9) 0.077(3) Uani 1 1 d . . .
H6 H 1.0042 0.3723 0.2655 0.093 Uiso 1 1 calc R . .
C7 C 0.8036(8) 0.6757(7) 0.0973(7) 0.0423(19) Uani 1 1 d . . .
C8 C 0.7002(9) 0.7673(7) 0.1262(8) 0.048(2) Uani 1 1 d . . .
C9 C 0.7149(10) 0.8493(7) 0.2533(9) 0.050(2) Uani 1 1 d . . .
C10 C 0.8194(10) 0.8749(8) 0.3766(10) 0.064(2) Uani 1 1 d . . .
H10 H 0.9032 0.8362 0.3894 0.077 Uiso 1 1 calc R . .
C11 C 0.7986(13) 0.9584(8) 0.4806(10) 0.090(3) Uani 1 1 d . . .
H11 H 0.8683 0.9778 0.5641 0.108 Uiso 1 1 calc R . .
C12 C 0.6701(13) 1.0127(9) 0.4569(11) 0.090(3) Uani 1 1 d . . .
H12 H 0.6562 1.0679 0.5276 0.108 Uiso 1 1 calc R . .
C13 C 0.5617(11) 0.9902(7) 0.3354(11) 0.078(3) Uani 1 1 d . . .
H13 H 0.4777 1.0287 0.3240 0.093 Uiso 1 1 calc R . .
C14 C 0.5856(11) 0.9063(7) 0.2304(11) 0.059(3) Uani 1 1 d . . .
C15 C 0.3542(10) 0.8990(8) 0.0380(9) 0.093(3) Uani 1 1 d . . .
H15A H 0.3259 0.8670 -0.0543 0.140 Uiso 1 1 calc R . .
H15B H 0.3669 0.9907 0.0656 0.140 Uiso 1 1 calc R . .
H15C H 0.2766 0.8633 0.0624 0.140 Uiso 1 1 calc R . .
C16 C 0.5686(10) 0.7786(7) 0.0382(8) 0.056(2) Uani 1 1 d . . .
H16 H 0.5331 0.7359 -0.0505 0.067 Uiso 1 1 calc R . .
C17 C 0.7594(7) 0.6098(7) -0.0478(7) 0.0367(18) Uani 1 1 d . . .
C18 C 0.7581(8) 0.6670(7) -0.1445(7) 0.0385(19) Uani 1 1 d . . .
C19 C 0.8010(8) 0.7911(7) -0.1414(8) 0.053(2) Uani 1 1 d . . .
H19 H 0.8376 0.8579 -0.0634 0.063 Uiso 1 1 calc R . .
C20 C 0.7888(9) 0.8140(9) -0.2542(10) 0.063(2) Uani 1 1 d . . .
H20 H 0.8169 0.8973 -0.2528 0.076 Uiso 1 1 calc R . .
C21 C 0.7354(10) 0.7158(10) -0.3708(10) 0.072(3) Uani 1 1 d . . .
H21 H 0.7288 0.7344 -0.4464 0.086 Uiso 1 1 calc R . .
C22 C 0.6918(8) 0.5914(8) -0.3778(8) 0.056(2) Uani 1 1 d . . .
H22 H 0.6542 0.5256 -0.4565 0.068 Uiso 1 1 calc R . .
C23 C 0.7062(8) 0.5683(7) -0.2633(8) 0.0414(19) Uani 1 1 d . . .
C24 C 0.6263(9) 0.3282(7) -0.3365(7) 0.065(2) Uani 1 1 d . . .
H24A H 0.5238 0.3194 -0.3919 0.098 Uiso 1 1 calc R . .
H24B H 0.6324 0.2642 -0.2938 0.098 Uiso 1 1 calc R . .
H24C H 0.6895 0.3172 -0.3874 0.098 Uiso 1 1 calc R . .
C25 C 0.7105(7) 0.4806(7) -0.1096(8) 0.043(2) Uani 1 1 d . . .
H25 H 0.7016 0.4195 -0.0691 0.051 Uiso 1 1 calc R . .
C26 C 0.9604(10) 0.7547(7) 0.1459(8) 0.048(2) Uani 1 1 d . . .
N1 N 0.4974(9) 0.8619(6) 0.1003(9) 0.066(2) Uani 1 1 d . . .
N2 N 0.6766(6) 0.4549(6) -0.2403(6) 0.0458(16) Uani 1 1 d . . .
N3 N 1.0757(8) 0.8138(7) 0.1805(7) 0.072(2) Uani 1 1 d . . .
Br1 Br 0.80468(13) 0.26272(10) 0.36924(12) 0.1097(6) 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
C1 C2 1.335(10) . ?
C1 C6 1.362(10) . ?
C1 Br1 1.863(7) . ?
C2 C3 1.379(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(9) . ?
C4 C7 1.547(9) . ?
C5 C6 1.367(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C26 1.508(11) . ?
C7 C17 1.526(9) . ?
C7 C8 1.522(9) . ?
C8 C16 1.378(9) . ?
C8 C9 1.450(10) . ?
C9 C10 1.382(10) . ?
C9 C14 1.419(10) . ?
C10 C11 1.381(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.406(11) . ?
C13 H13 0.9300 . ?
C14 N1 1.381(10) . ?
C15 N1 1.478(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N1 1.374(8) . ?
C16 H16 0.9300 . ?
C17 C25 1.370(9) . ?
C17 C18 1.417(9) . ?
C18 C19 1.383(9) . ?
C18 C23 1.400(9) . ?
C19 C20 1.359(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(9) . ?
C22 H22 0.9300 . ?
C23 N2 1.373(8) . ?
C24 N2 1.453(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 N2 1.372(8) . ?
C25 H25 0.9300 . ?
C26 N3 1.115(8) . ?

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
C2 C1 C6 120.1(7) . . ?
C2 C1 Br1 119.4(6) . . ?
C6 C1 Br1 120.5(6) . . ?
C1 C2 C3 121.1(7) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 120.9(7) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 115.9(7) . . ?
C5 C4 C7 122.8(6) . . ?
C3 C4 C7 121.2(7) . . ?
C6 C5 C4 122.2(7) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C1 C6 C5 119.8(7) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C26 C7 C17 107.3(6) . . ?
C26 C7 C8 107.3(6) . . ?
C17 C7 C8 111.7(6) . . ?
C26 C7 C4 107.9(6) . . ?
C17 C7 C4 110.8(5) . . ?
C8 C7 C4 111.6(6) . . ?
C16 C8 C9 107.7(7) . . ?
C16 C8 C7 126.1(7) . . ?
C9 C8 C7 125.9(8) . . ?
C10 C9 C14 121.6(9) . . ?
C10 C9 C8 134.0(9) . . ?
C14 C9 C8 104.4(8) . . ?
C11 C10 C9 119.6(9) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 118.2(11) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 124.6(10) . . ?
C13 C12 H12 117.7 . . ?
C11 C12 H12 117.7 . . ?
C12 C13 C14 116.5(10) . . ?
C12 C13 H13 121.8 . . ?
C14 C13 H13 121.8 . . ?
N1 C14 C13 130.3(9) . . ?
N1 C14 C9 110.1(8) . . ?
C13 C14 C9 119.5(10) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C8 110.2(7) . . ?
N1 C16 H16 124.9 . . ?
C8 C16 H16 124.9 . . ?
C25 C17 C18 106.7(7) . . ?
C25 C17 C7 125.2(7) . . ?
C18 C17 C7 128.1(6) . . ?
C19 C18 C23 119.0(7) . . ?
C19 C18 C17 133.7(8) . . ?
C23 C18 C17 107.2(6) . . ?
C20 C19 C18 119.0(8) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 121.2(8) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 121.5(8) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 117.2(8) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
N2 C23 C22 130.0(8) . . ?
N2 C23 C18 107.9(6) . . ?
C22 C23 C18 122.1(7) . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C25 C17 109.7(6) . . ?
N2 C25 H25 125.1 . . ?
C17 C25 H25 125.1 . . ?
N3 C26 C7 179.1(9) . . ?
C16 N1 C14 107.6(7) . . ?
C16 N1 C15 125.9(9) . . ?
C14 N1 C15 126.5(8) . . ?
C25 N2 C23 108.4(6) . . ?
C25 N2 C24 125.6(6) . . ?
C23 N2 C24 126.0(7) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.063
