# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1526711'
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H27 Br N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         547.43

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_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'
'-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                   11.8785(7)
_cell_length_b                   16.1043(11)
_cell_length_c                   27.3233(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5226.8(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8488
_cell_measurement_theta_min      2.2571
_cell_measurement_theta_max      23.7702
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2256

_exptl_absorpt_coefficient_mu    1.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.66

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            58212
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_full        27.13
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             5773
_reflns_number_gt                4205
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1187
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_number_reflns         5773
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+8.3392P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.578
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.22483(3) 0.04957(2) 0.65579(2) 0.02819(12) Uani d . . . 1 . .
C C1 -0.0410(3) 0.06568(18) 0.94173(12) 0.0181(7) Uani d . . . 1 . .
C C2 0.0153(3) 0.06512(18) 0.89080(12) 0.0172(7) Uani d . . . 1 . .
H H2 -0.0187 0.1095 0.8699 0.021 Uiso calc U . R 1 . .
C C3 0.1228(3) 0.10016(19) 0.91769(11) 0.0168(7) Uani d . . . 1 . .
C C4 0.2321(3) 0.05372(19) 0.91847(11) 0.0169(6) Uani d . . . 1 . .
C C5 0.2573(3) -0.0250(2) 0.93481(12) 0.0214(7) Uani d . . . 1 . .
H H5 0.201 -0.0595 0.9488 0.026 Uiso calc U . R 1 . .
C C6 0.3687(3) -0.0525(2) 0.93022(14) 0.0298(8) Uani d . . . 1 . .
H H6 0.3879 -0.1072 0.9401 0.036 Uiso calc U . R 1 . .
C C7 0.4507(3) -0.0008(2) 0.91141(14) 0.0314(9) Uani d . . . 1 . .
H H7 0.5258 -0.0206 0.9088 0.038 Uiso calc U . R 1 . .
C C8 0.4258(3) 0.0803(2) 0.89611(13) 0.0251(8) Uani d . . . 1 . .
H H8 0.4823 0.1161 0.8836 0.03 Uiso calc U . R 1 . .
C C9 0.3153(3) 0.10532(19) 0.90015(11) 0.0177(7) Uani d . . . 1 . .
C C10 0.1571(3) 0.18729(19) 0.89941(11) 0.0169(7) Uani d . . . 1 . .
C C11 0.0816(3) 0.13530(19) 1.00798(12) 0.0165(7) Uani d . . . 1 . .
C C12 0.2455(3) 0.2050(2) 1.04558(12) 0.0245(8) Uani d . . . 1 . .
C C13 0.2540(4) 0.1424(3) 1.08679(15) 0.0453(11) Uani d . . . 1 . .
H H13A 0.1799 0.135 1.1018 0.068 Uiso calc U . R 1 . .
H H13B 0.3074 0.1626 1.1114 0.068 Uiso calc U . R 1 . .
H H13C 0.2804 0.0892 1.0738 0.068 Uiso calc U . R 1 . .
C C14 0.3607(3) 0.2219(3) 1.02351(14) 0.0373(10) Uani d . . . 1 . .
H H14A 0.3919 0.1702 1.0103 0.056 Uiso calc U . R 1 . .
H H14B 0.411 0.2437 1.0489 0.056 Uiso calc U . R 1 . .
H H14C 0.3534 0.2627 0.9971 0.056 Uiso calc U . R 1 . .
C C15 0.1868(4) 0.2834(3) 1.05974(18) 0.0525(13) Uani d . . . 1 . .
H H15A 0.1802 0.3196 1.0311 0.079 Uiso calc U . R 1 . .
H H15B 0.23 0.3117 1.0853 0.079 Uiso calc U . R 1 . .
H H15C 0.1114 0.2702 1.0722 0.079 Uiso calc U . R 1 . .
C C16 0.0255(3) -0.01447(19) 0.86161(12) 0.0188(7) Uani d . . . 1 . .
H H16A 0.0725 -0.0547 0.8799 0.023 Uiso calc U . R 1 . .
H H16B -0.0501 -0.0393 0.8572 0.023 Uiso calc U . R 1 . .
C C17 0.0778(3) 0.0021(2) 0.81212(11) 0.0191(7) Uani d . . . 1 . .
C C18 0.0195(3) 0.0494(2) 0.77773(12) 0.0234(7) Uani d . . . 1 . .
H H18 -0.0518 0.0719 0.7863 0.028 Uiso calc U . R 1 . .
C C19 0.0622(3) 0.0645(2) 0.73165(12) 0.0239(8) Uani d . . . 1 . .
H H19 0.0213 0.0969 0.7087 0.029 Uiso calc U . R 1 . .
C C20 0.1658(3) 0.03148(19) 0.71974(12) 0.0195(7) Uani d . . . 1 . .
C C21 0.2271(3) -0.0149(2) 0.75297(13) 0.0245(7) Uani d . . . 1 . .
H H21 0.2987 -0.0367 0.7443 0.029 Uiso calc U . R 1 . .
C C22 0.1827(3) -0.0292(2) 0.79915(13) 0.0223(7) Uani d . . . 1 . .
H H22 0.2245 -0.0608 0.8222 0.027 Uiso calc U . R 1 . .
C C23 0.3348(3) 0.25653(19) 0.87414(12) 0.0197(7) Uani d . . . 1 . .
H H23A 0.402 0.2603 0.8955 0.024 Uiso calc U . R 1 . .
H H23B 0.2889 0.307 0.8798 0.024 Uiso calc U . R 1 . .
C C24 0.3731(3) 0.25579(19) 0.82123(12) 0.0203(7) Uani d . . . 1 . .
C C25 0.3018(3) 0.2297(2) 0.78373(13) 0.0265(8) Uani d . . . 1 . .
H H25 0.2305 0.2065 0.7915 0.032 Uiso calc U . R 1 . .
C C26 0.3339(4) 0.2373(2) 0.73550(14) 0.0364(9) Uani d . . . 1 . .
H H26 0.2839 0.2204 0.7103 0.044 Uiso calc U . R 1 . .
C C27 0.4383(4) 0.2693(2) 0.72356(15) 0.0409(10) Uani d . . . 1 . .
H H27 0.4598 0.2747 0.6902 0.049 Uiso calc U . R 1 . .
C C28 0.5106(3) 0.2933(2) 0.76000(15) 0.0366(10) Uani d . . . 1 . .
H H28 0.5828 0.3148 0.7519 0.044 Uiso calc U . R 1 . .
C C29 0.4785(3) 0.2863(2) 0.80881(14) 0.0268(8) Uani d . . . 1 . .
H H29 0.5293 0.3026 0.8339 0.032 Uiso calc U . R 1 . .
N N1 0.0546(2) 0.10141(16) 0.96275(9) 0.0160(6) Uani d . . . 1 . .
N N2 0.2691(2) 0.18400(15) 0.88867(10) 0.0178(6) Uani d . . . 1 . .
O O1 -0.13089(18) 0.04677(14) 0.95796(9) 0.0240(5) Uani d . . . 1 . .
O O2 0.01923(18) 0.13587(13) 1.04285(8) 0.0208(5) Uani d . . . 1 . .
O O3 0.18494(18) 0.16670(14) 1.00392(8) 0.0218(5) Uani d . . . 1 . .
O O4 0.09467(19) 0.24636(14) 0.89446(9) 0.0250(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C20 . 1.905(3) ?
C1 O1 . 1.196(4) ?
C1 N1 . 1.397(4) ?
C1 C2 . 1.544(4) ?
C2 C16 . 1.515(4) ?
C2 C3 . 1.578(4) ?
C2 H2 . 1.0 ?
C3 N1 . 1.474(4) ?
C3 C4 . 1.498(4) ?
C3 C10 . 1.544(4) ?
C4 C5 . 1.377(4) ?
C4 C9 . 1.386(4) ?
C5 C6 . 1.400(5) ?
C5 H5 . 0.95 ?
C6 C7 . 1.380(5) ?
C6 H6 . 0.95 ?
C7 C8 . 1.402(5) ?
C7 H7 . 0.95 ?
C8 C9 . 1.377(5) ?
C8 H8 . 0.95 ?
C9 N2 . 1.416(4) ?
C10 O4 . 1.213(4) ?
C10 N2 . 1.364(4) ?
C11 O2 . 1.207(4) ?
C11 O3 . 1.332(4) ?
C11 N1 . 1.389(4) ?
C12 O3 . 1.481(4) ?
C12 C15 . 1.493(5) ?
C12 C13 . 1.514(5) ?
C12 C14 . 1.520(5) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 C17 . 1.512(4) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C22 . 1.391(5) ?
C17 C18 . 1.394(5) ?
C18 C19 . 1.379(5) ?
C18 H18 . 0.95 ?
C19 C20 . 1.379(5) ?
C19 H19 . 0.95 ?
C20 C21 . 1.384(5) ?
C21 C22 . 1.387(5) ?
C21 H21 . 0.95 ?
C22 H22 . 0.95 ?
C23 N2 . 1.460(4) ?
C23 C24 . 1.516(5) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C29 . 1.387(5) ?
C24 C25 . 1.394(5) ?
C25 C26 . 1.377(5) ?
C25 H25 . 0.95 ?
C26 C27 . 1.382(6) ?
C26 H26 . 0.95 ?
C27 C28 . 1.371(6) ?
C27 H27 . 0.95 ?
C28 C29 . 1.392(5) ?
C28 H28 . 0.95 ?
C29 H29 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 132.7(3) ?
O1 C1 C2 . . 136.0(3) ?
N1 C1 C2 . . 91.2(2) ?
C16 C2 C1 . . 121.0(3) ?
C16 C2 C3 . . 118.9(3) ?
C1 C2 C3 . . 85.9(2) ?
C16 C2 H2 . . 109.7 ?
C1 C2 H2 . . 109.7 ?
C3 C2 H2 . . 109.7 ?
N1 C3 C4 . . 118.1(3) ?
N1 C3 C10 . . 113.7(2) ?
C4 C3 C10 . . 103.3(2) ?
N1 C3 C2 . . 87.1(2) ?
C4 C3 C2 . . 122.0(3) ?
C10 C3 C2 . . 112.8(3) ?
C5 C4 C9 . . 120.9(3) ?
C5 C4 C3 . . 130.8(3) ?
C9 C4 C3 . . 108.3(3) ?
C4 C5 C6 . . 117.9(3) ?
C4 C5 H5 . . 121.0 ?
C6 C5 H5 . . 121.0 ?
C7 C6 C5 . . 120.6(3) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 121.5(3) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C9 C8 C7 . . 116.7(3) ?
C9 C8 H8 . . 121.6 ?
C7 C8 H8 . . 121.6 ?
C8 C9 C4 . . 122.2(3) ?
C8 C9 N2 . . 127.9(3) ?
C4 C9 N2 . . 109.9(3) ?
O4 C10 N2 . . 127.0(3) ?
O4 C10 C3 . . 126.0(3) ?
N2 C10 C3 . . 107.0(3) ?
O2 C11 O3 . . 129.0(3) ?
O2 C11 N1 . . 124.3(3) ?
O3 C11 N1 . . 106.8(3) ?
O3 C12 C15 . . 108.9(3) ?
O3 C12 C13 . . 109.1(3) ?
C15 C12 C13 . . 113.6(3) ?
O3 C12 C14 . . 101.9(3) ?
C15 C12 C14 . . 111.8(3) ?
C13 C12 C14 . . 110.7(3) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C2 . . 110.8(3) ?
C17 C16 H16A . . 109.5 ?
C2 C16 H16A . . 109.5 ?
C17 C16 H16B . . 109.5 ?
C2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 108.1 ?
C22 C17 C18 . . 118.2(3) ?
C22 C17 C16 . . 122.2(3) ?
C18 C17 C16 . . 119.7(3) ?
C19 C18 C17 . . 121.9(3) ?
C19 C18 H18 . . 119.0 ?
C17 C18 H18 . . 119.0 ?
C20 C19 C18 . . 118.4(3) ?
C20 C19 H19 . . 120.8 ?
C18 C19 H19 . . 120.8 ?
C19 C20 C21 . . 121.6(3) ?
C19 C20 Br1 . . 119.1(2) ?
C21 C20 Br1 . . 119.4(2) ?
C20 C21 C22 . . 119.1(3) ?
C20 C21 H21 . . 120.4 ?
C22 C21 H21 . . 120.4 ?
C21 C22 C17 . . 120.8(3) ?
C21 C22 H22 . . 119.6 ?
C17 C22 H22 . . 119.6 ?
N2 C23 C24 . . 114.4(3) ?
N2 C23 H23A . . 108.7 ?
C24 C23 H23A . . 108.7 ?
N2 C23 H23B . . 108.7 ?
C24 C23 H23B . . 108.7 ?
H23A C23 H23B . . 107.6 ?
C29 C24 C25 . . 118.4(3) ?
C29 C24 C23 . . 120.1(3) ?
C25 C24 C23 . . 121.4(3) ?
C26 C25 C24 . . 120.5(3) ?
C26 C25 H25 . . 119.7 ?
C24 C25 H25 . . 119.7 ?
C25 C26 C27 . . 120.5(4) ?
C25 C26 H26 . . 119.8 ?
C27 C26 H26 . . 119.8 ?
C28 C27 C26 . . 119.7(4) ?
C28 C27 H27 . . 120.1 ?
C26 C27 H27 . . 120.1 ?
C27 C28 C29 . . 120.1(4) ?
C27 C28 H28 . . 119.9 ?
C29 C28 H28 . . 119.9 ?
C24 C29 C28 . . 120.7(4) ?
C24 C29 H29 . . 119.7 ?
C28 C29 H29 . . 119.7 ?
C11 N1 C1 . . 135.7(3) ?
C11 N1 C3 . . 128.4(2) ?
C1 N1 C3 . . 95.6(2) ?
C10 N2 C9 . . 111.4(3) ?
C10 N2 C23 . . 123.3(3) ?
C9 N2 C23 . . 124.7(3) ?
C11 O3 C12 . . 122.8(2) ?
