# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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/. 
# 
# Audit and citation data items have may 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_m1
_database_code_depnum_ccdc_archive 'CCDC 1019290'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2014-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H34 Br2 N2'
_chemical_formula_weight         534.37

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                   5.9858(5)
_cell_length_b                   10.0355(12)
_cell_length_c                   10.1711(12)
_cell_angle_alpha                93.862(10)
_cell_angle_beta                 91.455(9)
_cell_angle_gamma                96.575(9)
_cell_volume                     605.25(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1266
_cell_measurement_theta_max      26.3720
_cell_measurement_theta_min      3.4170

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             274
_exptl_absorpt_coefficient_mu    3.364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4319
_exptl_absorpt_correction_T_max  0.7297
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'multiwire proportional'
_diffrn_measurement_method       'phi 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            4235
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2385
_reflns_number_gt                2121
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0392P)²+0.2410P] 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_number_reflns         2385
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 1.03383(6) 1.25062(4) 0.00313(3) 0.04375(16) Uani 1 1 d . . .
N1 N 0.6217(4) 0.8387(2) 0.4661(2) 0.0205(5) Uani 1 1 d . . .
H1A H 0.6761 0.8292 0.5457 0.025 Uiso 1 1 calc R . .
C1 C 0.5070(4) 0.9555(3) 0.4355(3) 0.0196(6) Uani 1 1 d . . .
H1B H 0.3512 0.9233 0.4006 0.023 Uiso 1 1 calc R . .
C8 C 0.8700(5) 1.1655(3) 0.1384(3) 0.0249(6) Uani 1 1 d . . .
C2 C 0.6399(4) 0.7389(3) 0.3556(3) 0.0214(6) Uani 1 1 d . . .
H2A H 0.7280 0.7847 0.2858 0.026 Uiso 1 1 calc R . .
C9 C 0.5315(5) 1.0477(3) 0.2104(3) 0.0222(6) Uani 1 1 d . . .
H9A H 0.3787 1.0119 0.1937 0.027 Uiso 1 1 calc R . .
C10 C 0.6474(5) 1.1145(3) 0.1135(3) 0.0250(6) Uani 1 1 d . . .
H10A H 0.5751 1.1250 0.0313 0.030 Uiso 1 1 calc R . .
C11 C 0.8580(5) 1.0873(3) 0.3546(3) 0.0231(6) Uani 1 1 d . . .
H11A H 0.9304 1.0791 0.4374 0.028 Uiso 1 1 calc R . .
C3 C 0.4454(5) 0.5691(3) 0.1815(3) 0.0340(7) Uani 1 1 d . . .
H3A H 0.2963 0.5275 0.1460 0.041 Uiso 1 1 calc R . .
H3B H 0.5261 0.6130 0.1093 0.041 Uiso 1 1 calc R . .
C12 C 0.6340(4) 1.0321(2) 0.3315(3) 0.0181(5) Uani 1 1 d . . .
C13 C 0.9759(5) 1.1542(3) 0.2577(3) 0.0246(6) Uani 1 1 d . . .
H13A H 1.1280 1.1917 0.2740 0.029 Uiso 1 1 calc R . .
C4 C 0.7725(5) 0.6297(3) 0.4043(3) 0.0280(7) Uani 1 1 d . . .
H4A H 0.6921 0.5867 0.4771 0.034 Uiso 1 1 calc R . .
H4B H 0.9219 0.6713 0.4395 0.034 Uiso 1 1 calc R . .
C5 C 0.4138(5) 0.6752(3) 0.2932(3) 0.0294(7) Uani 1 1 d . . .
H5A H 0.3323 0.7462 0.2580 0.035 Uiso 1 1 calc R . .
H5B H 0.3212 0.6326 0.3617 0.035 Uiso 1 1 calc R . .
C6 C 0.8044(6) 0.5221(3) 0.2945(3) 0.0355(7) Uani 1 1 d . . .
H6A H 0.8814 0.4502 0.3316 0.043 Uiso 1 1 calc R . .
H6B H 0.9009 0.5628 0.2267 0.043 Uiso 1 1 calc R . .
C7 C 0.5778(6) 0.4611(3) 0.2304(4) 0.0393(8) Uani 1 1 d . . .
H7A H 0.6042 0.3972 0.1554 0.047 Uiso 1 1 calc R . .
H7B H 0.4890 0.4104 0.2954 0.047 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0445(2) 0.0525(3) 0.0329(2) 0.01507(16) 0.00989(15) -0.00900(16)
N1 0.0269(12) 0.0200(12) 0.0147(11) -0.0017(9) -0.0024(9) 0.0062(9)
C1 0.0212(13) 0.0183(13) 0.0188(14) 0.0000(11) 0.0007(10) 0.0014(11)
C8 0.0306(15) 0.0204(14) 0.0239(15) 0.0031(12) 0.0075(12) 0.0011(12)
C2 0.0250(14) 0.0168(14) 0.0222(14) -0.0002(11) 0.0036(11) 0.0023(11)
C9 0.0219(14) 0.0226(14) 0.0210(14) -0.0031(11) -0.0002(11) 0.0009(11)
C10 0.0314(16) 0.0247(15) 0.0184(14) -0.0001(12) -0.0002(12) 0.0026(12)
C11 0.0256(14) 0.0228(14) 0.0211(15) 0.0022(11) -0.0014(11) 0.0039(11)
C3 0.0339(17) 0.0305(16) 0.0350(18) -0.0121(14) 0.0010(14) 0.0014(13)
C12 0.0211(13) 0.0151(13) 0.0180(14) -0.0023(10) 0.0017(10) 0.0034(10)
C13 0.0181(13) 0.0257(15) 0.0299(16) 0.0035(12) 0.0022(11) 0.0010(11)
C4 0.0316(16) 0.0260(15) 0.0270(16) 0.0003(12) 0.0026(12) 0.0068(12)
C5 0.0257(15) 0.0268(16) 0.0348(17) -0.0080(13) 0.0004(12) 0.0055(12)
C6 0.0433(19) 0.0272(16) 0.0381(19) -0.0012(14) 0.0066(14) 0.0139(14)
C7 0.050(2) 0.0228(16) 0.043(2) -0.0098(14) 0.0085(16) 0.0005(14)

_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 C8 1.902(3) . ?
N1 C2 1.468(3) . ?
N1 C1 1.471(3) . ?
N1 H1A 0.8800 . ?
C1 C12 1.518(4) . ?
C1 C1 1.546(5) 2_676 ?
C1 H1B 1.0000 . ?
C8 C13 1.373(4) . ?
C8 C10 1.382(4) . ?
C2 C4 1.526(4) . ?
C2 C5 1.532(4) . ?
C2 H2A 1.0000 . ?
C9 C10 1.385(4) . ?
C9 C12 1.388(4) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C13 1.391(4) . ?
C11 C12 1.399(4) . ?
C11 H11A 0.9500 . ?
C3 C7 1.517(5) . ?
C3 C5 1.534(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C13 H13A 0.9500 . ?
C4 C6 1.531(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.533(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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 N1 C1 115.9(2) . . ?
C2 N1 H1A 122.1 . . ?
C1 N1 H1A 122.1 . . ?
N1 C1 C12 109.7(2) . . ?
N1 C1 C1 108.3(3) . 2_676 ?
C12 C1 C1 111.7(3) . 2_676 ?
N1 C1 H1B 109.0 . . ?
C12 C1 H1B 109.0 . . ?
C1 C1 H1B 109.0 2_676 . ?
C13 C8 C10 121.4(3) . . ?
C13 C8 Br1 119.4(2) . . ?
C10 C8 Br1 119.2(2) . . ?
N1 C2 C4 108.3(2) . . ?
N1 C2 C5 114.5(2) . . ?
C4 C2 C5 109.9(2) . . ?
N1 C2 H2A 108.0 . . ?
C4 C2 H2A 108.0 . . ?
C5 C2 H2A 108.0 . . ?
C10 C9 C12 121.3(2) . . ?
C10 C9 H9A 119.3 . . ?
C12 C9 H9A 119.3 . . ?
C8 C10 C9 119.0(3) . . ?
C8 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C13 C11 C12 120.7(2) . . ?
C13 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C7 C3 C5 111.0(3) . . ?
C7 C3 H3A 109.4 . . ?
C5 C3 H3A 109.4 . . ?
C7 C3 H3B 109.4 . . ?
C5 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C9 C12 C11 118.3(2) . . ?
C9 C12 C1 120.8(2) . . ?
C11 C12 C1 120.9(2) . . ?
C8 C13 C11 119.2(2) . . ?
C8 C13 H13A 120.4 . . ?
C11 C13 H13A 120.4 . . ?
C2 C4 C6 112.1(2) . . ?
C2 C4 H4A 109.2 . . ?
C6 C4 H4A 109.2 . . ?
C2 C4 H4B 109.2 . . ?
C6 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C2 C5 C3 111.6(2) . . ?
C2 C5 H5A 109.3 . . ?
C3 C5 H5A 109.3 . . ?
C2 C5 H5B 109.3 . . ?
C3 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C4 C6 C7 111.2(3) . . ?
C4 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C4 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C3 C7 C6 111.3(2) . . ?
C3 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C3 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.076
