# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1564733'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2018-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H25 Br N4 O6'
_chemical_formula_weight         605.44

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.443(9)
_cell_length_b                   6.804(4)
_cell_length_c                   17.163(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.801(15)
_cell_angle_gamma                90.00
_cell_volume                     1554.8(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    1.366
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  ?
_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            21199
_diffrn_reflns_av_R_equivalents  0.1491
_diffrn_reflns_av_sigmaI/netI    0.1358
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5412
_reflns_number_gt                3052
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1393P)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    mixed
_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   0.07(2)
_refine_ls_number_reflns         5412
_refine_ls_number_parameters     373
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_ref         0.2537
_refine_ls_wR_factor_gt          0.2282
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.98895(9) 0.8765(3) 0.57269(10) 0.1178(7) Uani 1 1 d . . .
N1 N 0.5594(5) 0.3786(9) 0.1695(4) 0.0405(14) Uani 1 1 d . . .
C1 C 0.8562(7) 0.8304(18) 0.4946(7) 0.072(3) Uani 1 1 d . . .
O1 O 0.6701(4) 0.6508(8) 0.2193(3) 0.0460(14) Uani 1 1 d . . .
O3 O 0.3248(5) 0.8238(9) 0.1896(3) 0.0577(15) Uani 1 1 d . . .
C18 C 0.6249(8) 0.1145(13) 0.1113(6) 0.062(3) Uani 1 1 d . . .
H18 H 0.6272 0.0358 0.1563 0.074 Uiso 1 1 calc R . .
C3 C 0.8185(7) 0.6426(15) 0.4906(6) 0.059(2) Uani 1 1 d . . .
H3 H 0.8590 0.5425 0.5232 0.071 Uiso 1 1 calc R . .
N3 N 0.2217(7) 0.7924(12) 0.1725(5) 0.069(2) Uani 1 1 d . . .
O2 O 0.7840(5) 0.4169(13) 0.2869(4) 0.076(2) Uani 1 1 d . . .
N2 N 0.4832(5) 0.2879(8) 0.1812(4) 0.0413(15) Uani 1 1 d . . .
C2 C 0.7983(9) 0.9758(17) 0.4453(8) 0.076(3) Uani 1 1 d . . .
H2 H 0.8254 1.1003 0.4464 0.092 Uiso 1 1 calc R . .
O4 O 0.4207(6) 0.8262(11) 0.4449(4) 0.0735(19) Uani 1 1 d . . .
N4 N 0.3335(7) 0.8039(9) 0.3988(5) 0.0537(19) Uani 1 1 d . . .
C4 C 0.6962(7) 0.9381(13) 0.3917(6) 0.060(2) Uani 1 1 d . . .
H4 H 0.6556 1.0387 0.3596 0.071 Uiso 1 1 calc R . .
O5 O 0.2635(7) 0.7818(11) 0.4208(5) 0.092(3) Uani 1 1 d . . .
C5 C 0.7203(6) 0.6042(11) 0.4382(5) 0.0422(19) Uani 1 1 d . . .
H5 H 0.6949 0.4778 0.4362 0.051 Uiso 1 1 calc R . .
C7 C 0.5499(6) 0.6973(10) 0.3374(5) 0.0321(16) Uani 1 1 d . . .
H7 H 0.5249 0.6361 0.3772 0.038 Uiso 1 1 calc R . .
C6 C 0.6583(7) 0.7508(12) 0.3880(6) 0.051(2) Uani 1 1 d . . .
C9 C 0.5938(6) 0.5300(11) 0.2220(5) 0.0396(18) Uani 1 1 d . . .
C8 C 0.5408(5) 0.5458(10) 0.2722(4) 0.0332(16) Uani 1 1 d . . .
C11 C 0.7684(7) 0.5782(18) 0.2599(6) 0.060(3) Uani 1 1 d . . .
C10 C 0.4713(5) 0.3913(10) 0.2440(4) 0.0326(15) Uani 1 1 d . . .
C13 C 0.5945(6) 0.3019(10) 0.1067(5) 0.0406(18) Uani 1 1 d . . .
C12 C 0.8407(9) 0.727(2) 0.2607(9) 0.101(4) Uani 1 1 d . . .
H12A H 0.8221 0.7806 0.2050 0.152 Uiso 1 1 calc R . .
H12B H 0.9063 0.6686 0.2784 0.152 Uiso 1 1 calc R . .
H12C H 0.8417 0.8296 0.2993 0.152 Uiso 1 1 calc R . .
C15 C 0.6255(8) 0.3519(18) -0.0182(6) 0.075(3) Uani 1 1 d . . .
H15 H 0.6272 0.4323 -0.0615 0.090 Uiso 1 1 calc R . .
C16 C 0.6519(9) 0.1623(18) -0.0159(6) 0.076(3) Uani 1 1 d . . .
H16 H 0.6700 0.1133 -0.0586 0.091 Uiso 1 1 calc R . .
C17 C 0.6531(9) 0.0378(14) 0.0478(7) 0.073(3) Uani 1 1 d . . .
H17 H 0.6720 -0.0931 0.0488 0.088 Uiso 1 1 calc R . .
C19 C 0.3876(5) 0.3412(9) 0.2704(4) 0.0353(16) Uani 1 1 d . . .
C20 C 0.4022(6) 0.3333(10) 0.3548(5) 0.0422(18) Uani 1 1 d . . .
H20 H 0.4659 0.3517 0.3966 0.051 Uiso 1 1 calc R . .
C21 C 0.3215(8) 0.2977(12) 0.3762(6) 0.055(2) Uani 1 1 d . . .
H21 H 0.3313 0.2930 0.4330 0.066 Uiso 1 1 calc R . .
C22 C 0.2287(8) 0.2697(13) 0.3172(7) 0.059(2) Uani 1 1 d . . .
H22 H 0.1750 0.2484 0.3333 0.070 Uiso 1 1 calc R . .
C23 C 0.2133(7) 0.2725(13) 0.2326(7) 0.059(3) Uani 1 1 d . . .
H23 H 0.1496 0.2497 0.1917 0.071 Uiso 1 1 calc R . .
C24 C 0.2925(7) 0.3092(11) 0.2090(5) 0.049(2) Uani 1 1 d . . .
H24 H 0.2823 0.3125 0.1520 0.058 Uiso 1 1 calc R . .
C25 C 0.4836(6) 0.8755(12) 0.3012(5) 0.0467(19) Uani 1 1 d . . .
H25A H 0.5015 0.9777 0.3439 0.056 Uiso 1 1 calc R . .
H25B H 0.4970 0.9253 0.2537 0.056 Uiso 1 1 calc R . .
C26 C 0.3780(6) 0.8355(10) 0.2737(5) 0.0404(18) Uani 1 1 d . . .
C27 C 0.3095(6) 0.8060(11) 0.3101(5) 0.0456(19) Uani 1 1 d . . .
C28 C 0.2153(8) 0.7814(12) 0.2459(7) 0.061(3) Uani 1 1 d . . .
C29 C 0.1139(8) 0.7508(18) 0.2506(10) 0.100(4) Uani 1 1 d . . .
H29A H 0.0625 0.7534 0.1947 0.150 Uiso 1 1 calc R . .
H29B H 0.1019 0.8536 0.2839 0.150 Uiso 1 1 calc R . .
H29C H 0.1130 0.6259 0.2764 0.150 Uiso 1 1 calc R . .
O7A O 0.8749(15) 0.660(5) 0.0313(8) 0.159(12) Uani 0.498(17) 1 d P A 1
O7B O 0.9091(9) 0.315(3) 0.1332(8) 0.096(7) Uani 0.502(17) 1 d P A 2
C14 C 0.5958(8) 0.4295(11) 0.0430(5) 0.055(2) Uani 1 1 d . . .
H14 H 0.5774 0.5608 0.0419 0.066 Uiso 1 1 calc R . .


_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 C1 1.892(10) . ?
N1 C9 1.331(10) . ?
N1 N2 1.343(9) . ?
N1 C13 1.454(9) . ?
C1 C2 1.358(16) . ?
C1 C3 1.381(15) . ?
O1 C9 1.390(9) . ?
O1 C11 1.407(12) . ?
O3 C26 1.349(9) . ?
O3 N3 1.417(11) . ?
C18 C13 1.340(11) . ?
C18 C17 1.403(13) . ?
C18 H18 0.9300 . ?
C3 C5 1.379(12) . ?
C3 H3 0.9300 . ?
N3 C28 1.300(12) . ?
O2 C11 1.179(12) . ?
N2 C10 1.353(9) . ?
C2 C4 1.427(14) . ?
C2 H2 0.9300 . ?
O4 N4 1.210(10) . ?
N4 O5 1.219(10) . ?
N4 C27 1.423(11) . ?
C4 C6 1.379(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(12) . ?
C5 H5 0.9300 . ?
C7 C8 1.489(10) . ?
C7 C6 1.512(12) . ?
C7 C25 1.520(11) . ?
C7 H7 0.9800 . ?
C9 C8 1.361(10) . ?
C8 C10 1.403(10) . ?
C11 C12 1.450(16) . ?
C10 C19 1.487(10) . ?
C13 C14 1.402(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C15 C16 1.341(16) . ?
C15 C14 1.384(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(15) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 C20 1.381(10) . ?
C19 C24 1.386(11) . ?
C20 C21 1.372(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.344(14) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(14) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(12) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.437(11) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.374(11) . ?
C27 C28 1.390(13) . ?
C28 C29 1.512(15) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C14 H14 0.9300 . ?

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
C9 N1 N2 111.5(6) . . ?
C9 N1 C13 129.3(6) . . ?
N2 N1 C13 119.1(6) . . ?
C2 C1 C3 120.5(9) . . ?
C2 C1 Br1 122.1(8) . . ?
C3 C1 Br1 117.4(10) . . ?
C9 O1 C11 116.0(7) . . ?
C26 O3 N3 110.4(6) . . ?
C13 C18 C17 119.7(9) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C5 C3 C1 119.6(10) . . ?
C5 C3 H3 120.2 . . ?
C1 C3 H3 120.2 . . ?
C28 N3 O3 105.7(7) . . ?
N1 N2 C10 104.1(5) . . ?
C1 C2 C4 120.2(9) . . ?
C1 C2 H2 119.9 . . ?
C4 C2 H2 119.9 . . ?
O4 N4 O5 126.2(8) . . ?
O4 N4 C27 117.4(8) . . ?
O5 N4 C27 116.4(9) . . ?
C6 C4 C2 119.2(9) . . ?
C6 C4 H4 120.4 . . ?
C2 C4 H4 120.4 . . ?
C3 C5 C6 121.3(8) . . ?
C3 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C8 C7 C6 111.6(6) . . ?
C8 C7 C25 112.8(6) . . ?
C6 C7 C25 113.0(6) . . ?
C8 C7 H7 106.3 . . ?
C6 C7 H7 106.3 . . ?
C25 C7 H7 106.3 . . ?
C4 C6 C5 119.1(9) . . ?
C4 C6 C7 123.5(8) . . ?
C5 C6 C7 117.2(7) . . ?
N1 C9 C8 109.6(7) . . ?
N1 C9 O1 121.8(6) . . ?
C8 C9 O1 128.5(7) . . ?
C9 C8 C10 103.0(6) . . ?
C9 C8 C7 128.5(6) . . ?
C10 C8 C7 128.4(6) . . ?
O2 C11 O1 121.5(8) . . ?
O2 C11 C12 128.3(11) . . ?
O1 C11 C12 110.2(11) . . ?
N2 C10 C8 111.8(6) . . ?
N2 C10 C19 119.5(6) . . ?
C8 C10 C19 128.6(6) . . ?
C18 C13 C14 122.1(7) . . ?
C18 C13 N1 119.8(7) . . ?
C14 C13 N1 118.0(7) . . ?
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 . . ?
C16 C15 C14 120.8(9) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 122.0(8) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C18 118.0(9) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C20 C19 C24 119.7(7) . . ?
C20 C19 C10 121.1(7) . . ?
C24 C19 C10 119.1(6) . . ?
C21 C20 C19 119.1(8) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C22 C21 C20 121.8(8) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 119.8(8) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.0(9) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 119.7(8) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
C26 C25 C7 113.8(6) . . ?
C26 C25 H25A 108.8 . . ?
C7 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
C7 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
O3 C26 C27 105.4(7) . . ?
O3 C26 C25 117.1(7) . . ?
C27 C26 C25 137.5(7) . . ?
C26 C27 C28 108.2(8) . . ?
C26 C27 N4 124.6(8) . . ?
C28 C27 N4 127.2(8) . . ?
N3 C28 C27 110.3(9) . . ?
N3 C28 C29 119.6(10) . . ?
C27 C28 C29 130.1(10) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C15 C14 C13 117.2(8) . . ?
C15 C14 H14 121.4 . . ?
C13 C14 H14 121.4 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.105
