# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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data_mo_d8v17545_0m
_database_code_depnum_ccdc_archive 'CCDC 1873098'
_audit_update_record             
;
2018-10-13 deposited with the CCDC.
2018-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          372-375
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Br N O6'
_chemical_formula_weight         372.17

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'
'-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                   10.1785(3)
_cell_length_b                   11.8901(4)
_cell_length_c                   25.9949(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3145.99(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      5.085
_cell_measurement_theta_max      51.396

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.641
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3875
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48093
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2925
_reflns_number_gt                2307
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0588P)²+3.9287P] 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     SHELXL
_refine_ls_extinction_coef       0.0136(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2925
_refine_ls_number_parameters     230
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_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
Br1 Br -0.05093(6) 0.89199(5) 0.25168(2) 0.0999(3) Uani 1 1 d . . . . .
N1 N 0.3464(3) 0.7624(3) 0.49391(10) 0.0563(7) Uani 1 1 d . . . . .
O1 O 0.1254(2) 0.83735(19) 0.44929(8) 0.0571(6) Uani 1 1 d . . . . .
O2 O 0.3457(2) 0.61642(18) 0.36697(8) 0.0524(6) Uani 1 1 d . . . . .
O3 O 0.3138(4) 0.7387(3) 0.53706(11) 0.0989(11) Uani 1 1 d . . . . .
O4 O 0.4189(3) 0.8399(2) 0.48270(11) 0.0756(8) Uani 1 1 d . . . . .
O5 O 0.6450(3) 0.6679(3) 0.35950(10) 0.0823(9) Uani 1 1 d . . . . .
C1 C 0.2498(3) 0.6757(3) 0.34273(12) 0.0496(7) Uani 1 1 d . . . . .
C2 C 0.2279(4) 0.6543(4) 0.29086(13) 0.0662(10) Uani 1 1 d . . . . .
H2 H 0.2753 0.5984 0.2741 0.079 Uiso 1 1 calc R U . . .
C3 C 0.1362(4) 0.7160(4) 0.26458(14) 0.0727(11) Uani 1 1 d . . . . .
H3 H 0.1216 0.7023 0.2298 0.087 Uiso 1 1 calc R U . . .
C4 C 0.0652(4) 0.7989(4) 0.28978(14) 0.0655(10) Uani 1 1 d . . . . .
C5 C 0.0814(3) 0.8179(3) 0.34134(14) 0.0566(8) Uani 1 1 d . . . . .
H5 H 0.0309 0.8718 0.3581 0.068 Uiso 1 1 calc R U . . .
C6 C 0.1744(3) 0.7555(3) 0.36842(12) 0.0468(7) Uani 1 1 d . . . . .
C7 C 0.1897(3) 0.7715(2) 0.42421(11) 0.0433(7) Uani 1 1 d . . . . .
C8 C 0.2916(3) 0.6942(2) 0.44958(11) 0.0426(7) Uani 1 1 d . . . . .
C9 C 0.4021(3) 0.6732(2) 0.41062(11) 0.0432(7) Uani 1 1 d . . . . .
H9 H 0.4377 0.7457 0.3994 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5136(3) 0.6002(3) 0.42953(12) 0.0476(7) Uani 1 1 d . . . . .
H10A H 0.5462 0.6294 0.4619 0.057 Uiso 1 1 calc R U . . .
H10B H 0.4817 0.5244 0.4354 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6236(3) 0.5971(3) 0.39099(13) 0.0583(9) Uani 1 1 d . . . . .
O6 O 0.6879(5) 0.4941(4) 0.3953(2) 0.0675(11) Uani 0.7 1 d D U P A 1
C12 C 0.8004(5) 0.4736(6) 0.3618(2) 0.0723(12) Uani 0.7 1 d D U P A 1
H12A H 0.7829 0.5038 0.3278 0.087 Uiso 0.7 1 calc R U P A 1
H12B H 0.8151 0.3933 0.3585 0.087 Uiso 0.7 1 calc R U P A 1
C13 C 0.9197(8) 0.5283(8) 0.3838(4) 0.0795(18) Uani 0.6 1 d D U P A 1
H13A H 0.9115 0.6084 0.3809 0.119 Uiso 0.6 1 calc R U P A 1
H13B H 0.9960 0.5037 0.3652 0.119 Uiso 0.6 1 calc R U P A 1
H13C H 0.9282 0.5078 0.4194 0.119 Uiso 0.6 1 calc R U P A 1
O6' O 0.7135(13) 0.5372(10) 0.4021(6) 0.0709(16) Uani 0.3 1 d D U P A 2
C12' C 0.8274(13) 0.5487(13) 0.3672(6) 0.0730(15) Uani 0.3 1 d D U P A 2
H12C H 0.8033 0.5298 0.3321 0.088 Uiso 0.3 1 calc R U P A 2
H12D H 0.8618 0.6248 0.3679 0.088 Uiso 0.3 1 calc R U P A 2
C13' C 0.9243(13) 0.4684(12) 0.3876(6) 0.082(2) Uani 0.4 1 d D U P A 2
H13D H 0.9411 0.4848 0.4231 0.122 Uiso 0.4 1 calc R U P A 2
H13E H 1.0046 0.4745 0.3684 0.122 Uiso 0.4 1 calc R U P A 2
H13F H 0.8905 0.3933 0.3845 0.122 Uiso 0.4 1 calc R U P A 2
C14 C 0.2258(4) 0.5880(3) 0.46935(14) 0.0574(9) Uani 1 1 d . . . . .
H14A H 0.1508 0.6079 0.4898 0.086 Uiso 1 1 calc R U . . .
H14B H 0.2870 0.5463 0.4900 0.086 Uiso 1 1 calc R U . . .
H14C H 0.1982 0.5427 0.4408 0.086 Uiso 1 1 calc R U . . .


_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 C4 1.898(4) . ?
N1 O3 1.203(4) . ?
N1 O4 1.216(4) . ?
N1 C8 1.515(4) . ?
O1 C7 1.210(4) . ?
O2 C1 1.359(4) . ?
O2 C9 1.440(3) . ?
O5 C11 1.194(4) . ?
C1 C2 1.390(4) . ?
C1 C6 1.392(5) . ?
C2 C3 1.369(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C5 C6 1.393(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.471(4) . ?
C7 C8 1.534(4) . ?
C8 C14 1.519(4) . ?
C8 C9 1.534(4) . ?
C9 C10 1.511(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.503(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O6' 1.196(15) . ?
C11 O6 1.394(6) . ?
O6 C12 1.459(6) . ?
C12 C13 1.491(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O6' C12' 1.480(14) . ?
C12' C13' 1.472(14) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
O3 N1 O4 124.6(3) . . ?
O3 N1 C8 118.9(3) . . ?
O4 N1 C8 116.5(3) . . ?
C1 O2 C9 114.1(2) . . ?
O2 C1 C2 118.1(3) . . ?
O2 C1 C6 121.8(3) . . ?
C2 C1 C6 120.1(3) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 Br1 119.3(3) . . ?
C3 C4 Br1 119.5(3) . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 C7 120.2(3) . . ?
C5 C6 C7 120.1(3) . . ?
O1 C7 C6 123.9(3) . . ?
O1 C7 C8 121.4(3) . . ?
C6 C7 C8 114.7(3) . . ?
N1 C8 C14 110.4(3) . . ?
N1 C8 C9 108.6(2) . . ?
C14 C8 C9 114.3(3) . . ?
N1 C8 C7 104.8(2) . . ?
C14 C8 C7 110.2(3) . . ?
C9 C8 C7 108.0(2) . . ?
O2 C9 C10 106.6(2) . . ?
O2 C9 C8 107.7(2) . . ?
C10 C9 C8 115.5(2) . . ?
O2 C9 H9 109.0 . . ?
C10 C9 H9 109.0 . . ?
C8 C9 H9 109.0 . . ?
C11 C10 C9 110.9(3) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O5 C11 O6' 116.5(7) . . ?
O5 C11 O6 126.0(4) . . ?
O5 C11 C10 125.2(3) . . ?
O6' C11 C10 115.0(7) . . ?
O6 C11 C10 108.5(3) . . ?
C11 O6 C12 117.9(5) . . ?
O6 C12 C13 109.7(6) . . ?
O6 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
O6 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
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 . . ?
C11 O6' C12' 113.3(12) . . ?
C13' C12' O6' 104.1(12) . . ?
C13' C12' H12C 110.9 . . ?
O6' C12' H12C 110.9 . . ?
C13' C12' H12D 110.9 . . ?
O6' C12' H12D 110.9 . . ?
H12C C12' H12D 109.0 . . ?
C12' C13' H13D 109.5 . . ?
C12' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O2 C1 C2 153.6(3) . . . . ?
C9 O2 C1 C6 -26.5(4) . . . . ?
O2 C1 C2 C3 -177.0(4) . . . . ?
C6 C1 C2 C3 3.1(6) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 -2.5(7) . . . . ?
C2 C3 C4 Br1 174.8(3) . . . . ?
C3 C4 C5 C6 2.5(6) . . . . ?
Br1 C4 C5 C6 -174.9(3) . . . . ?
O2 C1 C6 C5 177.0(3) . . . . ?
C2 C1 C6 C5 -3.2(5) . . . . ?
O2 C1 C6 C7 -5.0(5) . . . . ?
C2 C1 C6 C7 174.8(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C4 C5 C6 C7 -177.6(3) . . . . ?
C1 C6 C7 O1 -178.2(3) . . . . ?
C5 C6 C7 O1 -0.2(5) . . . . ?
C1 C6 C7 C8 -0.3(4) . . . . ?
C5 C6 C7 C8 177.7(3) . . . . ?
O3 N1 C8 C14 -12.9(4) . . . . ?
O4 N1 C8 C14 168.8(3) . . . . ?
O3 N1 C8 C9 -138.9(3) . . . . ?
O4 N1 C8 C9 42.8(4) . . . . ?
O3 N1 C8 C7 105.8(3) . . . . ?
O4 N1 C8 C7 -72.5(3) . . . . ?
O1 C7 C8 N1 -33.3(4) . . . . ?
C6 C7 C8 N1 148.8(3) . . . . ?
O1 C7 C8 C14 85.5(4) . . . . ?
C6 C7 C8 C14 -92.4(3) . . . . ?
O1 C7 C8 C9 -149.0(3) . . . . ?
C6 C7 C8 C9 33.1(3) . . . . ?
C1 O2 C9 C10 -175.1(3) . . . . ?
C1 O2 C9 C8 60.4(3) . . . . ?
N1 C8 C9 O2 -175.4(2) . . . . ?
C14 C8 C9 O2 60.8(3) . . . . ?
C7 C8 C9 O2 -62.3(3) . . . . ?
N1 C8 C9 C10 65.6(3) . . . . ?
C14 C8 C9 C10 -58.2(4) . . . . ?
C7 C8 C9 C10 178.7(2) . . . . ?
O2 C9 C10 C11 67.6(3) . . . . ?
C8 C9 C10 C11 -172.9(3) . . . . ?
C9 C10 C11 O5 24.3(5) . . . . ?
C9 C10 C11 O6' -177.0(7) . . . . ?
C9 C10 C11 O6 -150.4(3) . . . . ?
O5 C11 O6 C12 6.4(7) . . . . ?
O6' C11 O6 C12 -69.5(19) . . . . ?
C10 C11 O6 C12 -179.0(4) . . . . ?
C11 O6 C12 C13 81.2(7) . . . . ?
O5 C11 O6' C12' -11.2(14) . . . . ?
O6 C11 O6' C12' 108(2) . . . . ?
C10 C11 O6' C12' -171.8(10) . . . . ?
C11 O6' C12' C13' -179.7(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14A O4 0.96 2.54 3.471(5) 162.6 4_466
C10 H10B O1 0.97 2.50 3.469(4) 173.8 8_655
C10 H10A O1 0.97 2.48 3.431(4) 168.0 4_566
C3 H3 O5 0.93 2.37 3.277(5) 165.0 6_556

_refine_diff_density_max         0.978
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
