# 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_shelxl2_a
_database_code_depnum_ccdc_archive 'CCDC 1063974'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Br N O3'
_chemical_formula_weight         476.35

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.2811(10)
_cell_length_b                   7.9645(12)
_cell_length_c                   11.2853(18)
_cell_angle_alpha                71.7010(10)
_cell_angle_beta                 89.752(2)
_cell_angle_gamma                81.716(2)
_cell_volume                     529.91(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    90
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.968
_shelx_estimated_absorpt_T_min   0.827
_shelx_estimated_absorpt_T_max   0.827
_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            5764
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.902
_diffrn_reflns_theta_max         27.438
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_point_group_measured_fraction_full 0.915
_reflns_number_total             4318
_reflns_number_gt                4274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_max     0.807
_reflns_Friedel_fraction_full    0.838

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 1902 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4318
_refine_ls_number_parameters     281
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0193
_refine_ls_wR_factor_ref         0.0470
_refine_ls_wR_factor_gt          0.0469
_refine_ls_goodness_of_fit_ref   0.675
_refine_ls_restrained_S_all      0.674
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.96405(3) 1.42459(3) 0.05872(2) 0.01952(7) Uani 1 1 d . . . . .
C1 C 0.4039(5) -0.2851(4) 0.8528(3) 0.0134(6) Uani 1 1 d . . . . .
C2 C 0.2917(5) -0.1001(3) 0.8497(2) 0.0113(5) Uani 1 1 d . . . . .
C3 C 0.4308(4) -0.0441(3) 0.9403(2) 0.0153(5) Uani 1 1 d . . . . .
H3A H 0.3906 -0.1006 1.0271 0.018 Uiso 1 1 calc R U . . .
H3B H 0.5843 -0.0890 0.9337 0.018 Uiso 1 1 calc R U . . .
C4 C 0.4027(4) 0.1573(3) 0.9127(2) 0.0178(5) Uani 1 1 d . . . . .
H4A H 0.5007 0.1866 0.9692 0.021 Uiso 1 1 calc R U . . .
H4B H 0.2530 0.2012 0.9283 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4514(4) 0.2503(4) 0.7776(2) 0.0163(5) Uani 1 1 d . . . . .
H5A H 0.4317 0.3814 0.7610 0.020 Uiso 1 1 calc R U . . .
H5B H 0.6027 0.2104 0.7623 0.020 Uiso 1 1 calc R U . . .
C6 C 0.3153(4) 0.0159(3) 0.7124(2) 0.0112(4) Uani 1 1 d . . . . .
H6 H 0.1927 0.0026 0.6614 0.013 Uiso 1 1 calc R U . . .
C7 C 0.5206(4) -0.0792(3) 0.6748(2) 0.0126(5) Uani 1 1 d . . . . .
C8 C 0.6538(4) -0.0168(3) 0.5773(2) 0.0169(5) Uani 1 1 d . . . . .
H8 H 0.6265 0.1036 0.5240 0.020 Uiso 1 1 calc R U . . .
C9 C 0.8275(4) -0.1334(4) 0.5591(2) 0.0216(6) Uani 1 1 d . . . . .
H9 H 0.9201 -0.0919 0.4930 0.026 Uiso 1 1 calc R U . . .
C10 C 0.8689(4) -0.3119(4) 0.6369(3) 0.0214(6) Uani 1 1 d . . . . .
H10 H 0.9883 -0.3899 0.6225 0.026 Uiso 1 1 calc R U . . .
C11 C 0.7373(4) -0.3752(3) 0.7344(3) 0.0183(5) Uani 1 1 d . . . . .
H11 H 0.7641 -0.4959 0.7871 0.022 Uiso 1 1 calc R U . . .
C12 C 0.5636(4) -0.2566(3) 0.7533(2) 0.0134(5) Uani 1 1 d . . . . .
C13 C 0.0578(4) -0.0977(3) 0.8867(2) 0.0159(5) Uani 1 1 d . . . . .
H13A H -0.0245 -0.1339 0.8277 0.024 Uiso 1 1 calc R U . . .
H13B H -0.0037 0.0234 0.8850 0.024 Uiso 1 1 calc R U . . .
H13C H 0.0513 -0.1810 0.9711 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2650(4) 0.3245(3) 0.5714(2) 0.0130(5) Uani 1 1 d . . . . .
C15 C 0.3919(4) 0.4580(3) 0.5177(2) 0.0141(5) Uani 1 1 d . . . . .
H15 H 0.5132 0.4697 0.5629 0.017 Uiso 1 1 calc R U . . .
C16 C 0.3375(4) 0.5731(3) 0.3973(2) 0.0147(5) Uani 1 1 d . . . . .
C17 C 0.1645(4) 0.5618(3) 0.3273(2) 0.0167(5) Uani 1 1 d . . . . .
H17 H 0.1334 0.6402 0.2445 0.020 Uiso 1 1 calc R U . . .
C18 C 0.0362(4) 0.4309(3) 0.3824(2) 0.0164(5) Uani 1 1 d . . . . .
H18 H -0.0864 0.4221 0.3370 0.020 Uiso 1 1 calc R U . . .
C19 C 0.0848(4) 0.3142(3) 0.5018(2) 0.0145(5) Uani 1 1 d . . . . .
H19 H -0.0044 0.2261 0.5373 0.017 Uiso 1 1 calc R U . . .
C20 C 0.4033(4) 0.8703(3) 0.3428(2) 0.0151(5) Uani 1 1 d . . . . .
C21 C 0.5422(4) 1.0006(4) 0.2720(2) 0.0127(5) Uani 1 1 d . . . . .
C22 C 0.7369(5) 0.9464(3) 0.2251(2) 0.0156(5) Uani 1 1 d . . . . .
H22 H 0.7830 0.8232 0.2364 0.019 Uiso 1 1 calc R U . . .
C23 C 0.8630(4) 1.0732(3) 0.1618(2) 0.0171(5) Uani 1 1 d . . . . .
H23 H 0.9963 1.0378 0.1301 0.020 Uiso 1 1 calc R U . . .
C24 C 0.7907(4) 1.2534(3) 0.1456(2) 0.0153(5) Uani 1 1 d . . . . .
C25 C 0.5965(5) 1.3086(4) 0.1913(3) 0.0153(6) Uani 1 1 d . . . . .
H25 H 0.5487 1.4319 0.1786 0.018 Uiso 1 1 calc R U . . .
C26 C 0.4736(5) 1.1799(4) 0.2559(3) 0.0162(6) Uani 1 1 d . . . . .
H26 H 0.3417 1.2151 0.2891 0.019 Uiso 1 1 calc R U . . .
N1 N 0.3065(3) 0.2070(3) 0.69435(18) 0.0125(4) Uani 1 1 d . . . . .
O1 O 0.3727(4) -0.4266(3) 0.9261(2) 0.0206(5) Uani 1 1 d . . . . .
O2 O 0.4740(3) 0.7001(2) 0.34256(17) 0.0179(4) Uani 1 1 d . . . . .
O3 O 0.2461(3) 0.9083(3) 0.3953(2) 0.0268(5) 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
Br01 C24 1.893(2) . ?
C1 O1 1.213(4) . ?
C1 C12 1.488(4) . ?
C1 C2 1.529(4) . ?
C2 C13 1.524(4) . ?
C2 C3 1.553(3) . ?
C2 C6 1.555(3) . ?
C3 C4 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.523(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.460(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.464(3) . ?
C6 C7 1.527(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.388(3) . ?
C7 C12 1.400(3) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(4) . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.404(3) . ?
C14 C19 1.407(3) . ?
C14 N1 1.409(3) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(4) . ?
C16 O2 1.411(3) . ?
C17 C18 1.397(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O3 1.199(3) . ?
C20 O2 1.365(3) . ?
C20 C21 1.487(4) . ?
C21 C26 1.385(4) . ?
C21 C22 1.396(4) . ?
C22 C23 1.389(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(4) . ?
C25 C26 1.390(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
O1 C1 C12 127.2(3) . . ?
O1 C1 C2 125.8(3) . . ?
C12 C1 C2 106.9(2) . . ?
C13 C2 C1 113.4(2) . . ?
C13 C2 C3 111.9(2) . . ?
C1 C2 C3 104.9(2) . . ?
C13 C2 C6 112.8(2) . . ?
C1 C2 C6 102.7(2) . . ?
C3 C2 C6 110.4(2) . . ?
C4 C3 C2 112.5(2) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C5 110.8(2) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C4 109.4(2) . . ?
N1 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 C7 116.69(19) . . ?
N1 C6 C2 114.34(19) . . ?
C7 C6 C2 103.18(19) . . ?
N1 C6 H6 107.4 . . ?
C7 C6 H6 107.4 . . ?
C2 C6 H6 107.4 . . ?
C8 C7 C12 120.1(2) . . ?
C8 C7 C6 129.8(2) . . ?
C12 C7 C6 110.0(2) . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 118.2(2) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 C1 129.8(2) . . ?
C7 C12 C1 108.9(2) . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.5(2) . . ?
C15 C14 N1 122.1(2) . . ?
C19 C14 N1 119.4(2) . . ?
C16 C15 C14 119.0(2) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 123.0(2) . . ?
C17 C16 O2 118.9(2) . . ?
C15 C16 O2 118.1(2) . . ?
C16 C17 C18 117.7(2) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
O3 C20 O2 122.9(2) . . ?
O3 C20 C21 124.4(2) . . ?
O2 C20 C21 112.7(2) . . ?
C26 C21 C22 120.5(3) . . ?
C26 C21 C20 117.5(2) . . ?
C22 C21 C20 122.0(2) . . ?
C23 C22 C21 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 119.0(2) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 121.6(2) . . ?
C25 C24 Br01 119.9(2) . . ?
C23 C24 Br01 118.48(19) . . ?
C24 C25 C26 118.7(3) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C21 C26 C25 120.4(3) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C14 N1 C5 118.72(19) . . ?
C14 N1 C6 116.93(19) . . ?
C5 N1 C6 115.13(19) . . ?
C20 O2 C16 115.51(19) . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

