# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc20yk8t
_database_code_depnum_ccdc_archive 'CCDC 1875446'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H26 Br N3 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         528.40
_chemical_absolute_configuration rm

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.436(7)
_cell_length_b                   13.238(12)
_cell_length_c                   25.73(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2533.(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    177
_cell_measurement_theta_min      3.1454
_cell_measurement_theta_max      20.2243
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.209
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088

_exptl_absorpt_coefficient_mu    1.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.517
_exptl_absorpt_correction_T_max  0.707

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       ω

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13792
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         26.94
_diffrn_reflns_theta_full        26.94
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28

_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.
;

_reflns_number_total             5376
_reflns_number_gt                3612
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1239
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_number_reflns         5376
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.466
_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   0.014(10)

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       'Bruker Instrument Service v2010.11.0.0'
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.72302(8) 1.37676(4) 0.57871(2) 0.0897(2) Uani d . 1 . .
O O1 0.7092(3) 0.96708(15) 0.41995(8) 0.0381(5) Uani d . 1 . .
O O2 0.7502(6) 1.08575(19) 0.35887(9) 0.0717(10) Uani d . 1 . .
O O3 0.0802(3) 0.81296(19) 0.32230(9) 0.0422(6) Uani d . 1 . .
O O4 0.2516(5) 0.55555(18) 0.40222(10) 0.0636(8) Uani d . 1 . .
O O5 0.4521(3) 0.7834(2) 0.27682(8) 0.0435(6) Uani d . 1 . .
N N1 0.1072(4) 0.6470(2) 0.33737(10) 0.0376(7) Uani d . 1 . .
N N2 -0.0267(4) 0.6296(2) 0.29925(11) 0.0457(8) Uani d . 1 . .
H H2 -0.0892 0.674 0.2828 0.055 Uiso calc R 1 . .
N N3 0.5813(4) 0.7819(2) 0.31945(10) 0.0353(7) Uani d . 1 . .
C C1 0.7221(7) 1.2775(3) 0.52506(16) 0.0601(11) Uani d . 1 . .
C C2 0.7256(8) 1.1784(3) 0.53750(15) 0.0695(14) Uani d . 1 . .
H H1 0.7261 1.1586 0.5722 0.083 Uiso calc R 1 . .
C C3 0.7283(6) 1.1060(3) 0.49844(13) 0.0547(10) Uani d . 1 . .
H H3 0.7316 1.0377 0.5069 0.066 Uiso calc R 1 . .
C C4 0.7261(5) 1.1356(2) 0.44752(13) 0.0431(8) Uani d . 1 . .
C C5 0.7316(5) 1.0622(2) 0.40371(14) 0.0424(8) Uani d . 1 . .
C C6 0.7252(5) 0.8867(2) 0.38025(11) 0.0338(7) Uani d . 1 . .
H H6 0.832 0.8991 0.3589 0.041 Uiso calc R 1 . .
C C7 0.5620(5) 0.8811(2) 0.34590(12) 0.0374(8) Uani d . 1 . .
H H7 0.5616 0.9364 0.3206 0.045 Uiso calc R 1 . .
C C8 0.3817(4) 0.8775(3) 0.37664(13) 0.0351(7) Uani d . 1 . .
H H8A 0.3977 0.9035 0.4116 0.042 Uiso calc R 1 . .
H H8B 0.29 0.9172 0.3592 0.042 Uiso calc R 1 . .
C C9 0.3296(4) 0.7661(2) 0.37791(12) 0.0311(7) Uani d . 1 . .
H H9 0.3039 0.7454 0.4137 0.037 Uiso calc R 1 . .
C C10 0.1661(5) 0.7466(3) 0.34377(12) 0.0350(8) Uani d . 1 . .
C C11 -0.0354(6) 0.5183(3) 0.29394(14) 0.0485(10) Uani d . 1 . .
C C12 0.1058(7) 0.4860(3) 0.25437(16) 0.0631(13) Uani d . 1 . .
H H12A 0.0817 0.5181 0.2216 0.095 Uiso calc R 1 . .
H H12B 0.1018 0.414 0.2501 0.095 Uiso calc R 1 . .
H H12C 0.2229 0.5056 0.2664 0.095 Uiso calc R 1 . .
C C13 0.7209(8) 1.3090(3) 0.47480(17) 0.0698(13) Uani d . 1 . .
H H13 0.7166 1.3776 0.467 0.084 Uiso calc R 1 . .
C C14 0.7260(7) 1.2378(3) 0.43532(15) 0.0647(12) Uani d . 1 . .
H H14 0.7294 1.2584 0.4008 0.078 Uiso calc R 1 . .
C C15 -0.2223(7) 0.4867(3) 0.27701(18) 0.0730(13) Uani d . 1 . .
H H15A -0.3085 0.5086 0.3024 0.11 Uiso calc R 1 . .
H H15B -0.2272 0.4144 0.2739 0.11 Uiso calc R 1 . .
H H15C -0.2497 0.5169 0.244 0.11 Uiso calc R 1 . .
C C16 0.0172(6) 0.4798(3) 0.34748(15) 0.0497(10) Uani d . 1 . .
H H16A -0.0873 0.4727 0.3697 0.06 Uiso calc R 1 . .
H H16B 0.0786 0.4153 0.3452 0.06 Uiso calc R 1 . .
C C17 0.1416(6) 0.5612(3) 0.36738(14) 0.0443(9) Uani d . 1 . .
C C18 0.5013(4) 0.7134(2) 0.35858(12) 0.0312(7) Uani d . 1 . .
H H18 0.4748 0.6469 0.3438 0.037 Uiso calc R 1 . .
C C19 0.5350(7) 0.7460(4) 0.23196(14) 0.0781(17) Uani d . 1 . .
H H19A 0.627 0.7921 0.2209 0.117 Uiso calc R 1 . .
H H19B 0.447 0.7388 0.2049 0.117 Uiso calc R 1 . .
H H19C 0.5879 0.6814 0.2393 0.117 Uiso calc R 1 . .
C C20 0.6434(4) 0.7067(2) 0.40098(12) 0.0319(7) Uani d . 1 . .
C C21 0.6706(5) 0.6194(3) 0.43026(12) 0.0416(8) Uani d . 1 . .
H H21 0.5985 0.5633 0.4239 0.05 Uiso calc R 1 . .
C C22 0.7985(6) 0.6136(3) 0.46759(13) 0.0510(10) Uani d . 1 . .
H H22 0.8104 0.5551 0.4873 0.061 Uiso calc R 1 . .
C C23 0.9124(6) 0.6955(3) 0.47647(13) 0.0456(9) Uani d . 1 . .
H H23 1.0039 0.6905 0.501 0.055 Uiso calc R 1 . .
C C24 0.8891(5) 0.7842(3) 0.44887(13) 0.0432(9) Uani d . 1 . .
H H24 0.9634 0.8394 0.4551 0.052 Uiso calc R 1 . .
C C25 0.7513(4) 0.7901(2) 0.41110(11) 0.0326(7) 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 C1 . 1.906(4) ?
O1 C5 . 1.337(4) ?
O1 C6 . 1.480(3) ?
O2 C5 . 1.203(4) ?
O3 C10 . 1.218(4) ?
O4 C17 . 1.216(5) ?
O5 C19 . 1.399(4) ?
O5 N3 . 1.458(3) ?
N1 C17 . 1.396(5) ?
N1 C10 . 1.400(4) ?
N1 N2 . 1.417(4) ?
N2 C11 . 1.482(5) ?
N2 H2 . 0.86 ?
N3 C18 . 1.480(4) ?
N3 C7 . 1.486(4) ?
C1 C2 . 1.351(6) ?
C1 C13 . 1.359(6) ?
C2 C3 . 1.388(5) ?
C2 H1 . 0.93 ?
C3 C4 . 1.367(5) ?
C3 H3 . 0.93 ?
C4 C14 . 1.389(5) ?
C4 C5 . 1.489(5) ?
C6 C7 . 1.503(5) ?
C6 C25 . 1.518(4) ?
C6 H6 . 0.98 ?
C7 C8 . 1.558(5) ?
C7 H7 . 0.98 ?
C8 C9 . 1.526(5) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 C10 . 1.521(5) ?
C9 C18 . 1.537(5) ?
C9 H9 . 0.98 ?
C11 C15 . 1.516(6) ?
C11 C16 . 1.520(6) ?
C11 C12 . 1.524(6) ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 C14 . 1.386(5) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 C17 . 1.510(5) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C18 C20 . 1.522(5) ?
C18 H18 . 0.98 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 C25 . 1.389(4) ?
C20 C21 . 1.395(5) ?
C21 C22 . 1.354(5) ?
C21 H21 . 0.93 ?
C22 C23 . 1.394(6) ?
C22 H22 . 0.93 ?
C23 C24 . 1.383(5) ?
C23 H23 . 0.93 ?
C24 C25 . 1.415(5) ?
C24 H24 . 0.93 ?

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
C5 O1 C6 . . 116.8(2) ?
C19 O5 N3 . . 109.0(3) ?
C17 N1 C10 . . 130.1(3) ?
C17 N1 N2 . . 112.3(3) ?
C10 N1 N2 . . 117.0(3) ?
N1 N2 C11 . . 104.8(3) ?
N1 N2 H2 . . 127.6 ?
C11 N2 H2 . . 127.6 ?
O5 N3 C18 . . 104.8(2) ?
O5 N3 C7 . . 105.6(2) ?
C18 N3 C7 . . 101.0(2) ?
C2 C1 C13 . . 121.6(3) ?
C2 C1 Br1 . . 119.9(3) ?
C13 C1 Br1 . . 118.6(3) ?
C1 C2 C3 . . 119.9(4) ?
C1 C2 H1 . . 120.0 ?
C3 C2 H1 . . 120.0 ?
C4 C3 C2 . . 119.7(4) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C14 . . 119.7(3) ?
C3 C4 C5 . . 122.6(3) ?
C14 C4 C5 . . 117.7(3) ?
O2 C5 O1 . . 123.9(3) ?
O2 C5 C4 . . 124.1(3) ?
O1 C5 C4 . . 112.0(3) ?
O1 C6 C7 . . 112.1(3) ?
O1 C6 C25 . . 104.8(2) ?
C7 C6 C25 . . 111.6(3) ?
O1 C6 H6 . . 109.4 ?
C7 C6 H6 . . 109.4 ?
C25 C6 H6 . . 109.4 ?
N3 C7 C6 . . 103.6(3) ?
N3 C7 C8 . . 106.8(3) ?
C6 C7 C8 . . 113.5(3) ?
N3 C7 H7 . . 110.9 ?
C6 C7 H7 . . 110.9 ?
C8 C7 H7 . . 110.9 ?
C9 C8 C7 . . 105.0(3) ?
C9 C8 H8A . . 110.8 ?
C7 C8 H8A . . 110.8 ?
C9 C8 H8B . . 110.8 ?
C7 C8 H8B . . 110.8 ?
H8A C8 H8B . . 108.8 ?
C10 C9 C8 . . 110.7(3) ?
C10 C9 C18 . . 113.6(3) ?
C8 C9 C18 . . 102.8(3) ?
C10 C9 H9 . . 109.8 ?
C8 C9 H9 . . 109.8 ?
C18 C9 H9 . . 109.8 ?
O3 C10 N1 . . 117.5(3) ?
O3 C10 C9 . . 124.0(3) ?
N1 C10 C9 . . 118.5(3) ?
N2 C11 C15 . . 109.9(3) ?
N2 C11 C16 . . 103.8(3) ?
C15 C11 C16 . . 113.8(4) ?
N2 C11 C12 . . 108.1(3) ?
C15 C11 C12 . . 111.3(3) ?
C16 C11 C12 . . 109.5(4) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C1 C13 C14 . . 119.3(4) ?
C1 C13 H13 . . 120.4 ?
C14 C13 H13 . . 120.4 ?
C13 C14 C4 . . 119.8(4) ?
C13 C14 H14 . . 120.1 ?
C4 C14 H14 . . 120.1 ?
C11 C15 H15A . . 109.5 ?
C11 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C11 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C11 . . 103.1(3) ?
C17 C16 H16A . . 111.2 ?
C11 C16 H16A . . 111.2 ?
C17 C16 H16B . . 111.2 ?
C11 C16 H16B . . 111.2 ?
H16A C16 H16B . . 109.1 ?
O4 C17 N1 . . 125.5(3) ?
O4 C17 C16 . . 128.1(3) ?
N1 C17 C16 . . 106.3(3) ?
N3 C18 C20 . . 104.1(3) ?
N3 C18 C9 . . 106.1(3) ?
C20 C18 C9 . . 111.8(2) ?
N3 C18 H18 . . 111.5 ?
C20 C18 H18 . . 111.5 ?
C9 C18 H18 . . 111.5 ?
O5 C19 H19A . . 109.5 ?
O5 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O5 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C25 C20 C21 . . 118.3(3) ?
C25 C20 C18 . . 119.3(3) ?
C21 C20 C18 . . 122.4(3) ?
C22 C21 C20 . . 122.1(3) ?
C22 C21 H21 . . 119.0 ?
C20 C21 H21 . . 119.0 ?
C21 C22 C23 . . 120.0(3) ?
C21 C22 H22 . . 120.0 ?
C23 C22 H22 . . 120.0 ?
C24 C23 C22 . . 120.0(3) ?
C24 C23 H23 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C23 C24 C25 . . 119.4(3) ?
C23 C24 H24 . . 120.3 ?
C25 C24 H24 . . 120.3 ?
C20 C25 C24 . . 120.2(3) ?
C20 C25 C6 . . 119.8(3) ?
C24 C25 C6 . . 119.9(3) ?

